GB811780A - Hydrazides and thiosemicarbazones - Google Patents
Hydrazides and thiosemicarbazonesInfo
- Publication number
- GB811780A GB811780A GB20288/55A GB2028855A GB811780A GB 811780 A GB811780 A GB 811780A GB 20288/55 A GB20288/55 A GB 20288/55A GB 2028855 A GB2028855 A GB 2028855A GB 811780 A GB811780 A GB 811780A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- hydrazine hydrate
- ethanol
- diethyl ester
- refluxed
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 title abstract 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 title abstract 2
- 150000003584 thiosemicarbazones Chemical class 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 9
- FPXRIICLDFIBCR-UHFFFAOYSA-N Cl.C(CCCCC(=O)O)(=O)NN Chemical compound Cl.C(CCCCC(=O)O)(=O)NN FPXRIICLDFIBCR-UHFFFAOYSA-N 0.000 abstract 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 238000010992 reflux Methods 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 abstract 2
- MJQOJHICLSTPBF-VKHMYHEASA-N (2s)-2-aminopentanedihydrazide Chemical compound NNC(=O)CC[C@H](N)C(=O)NN MJQOJHICLSTPBF-VKHMYHEASA-N 0.000 abstract 1
- UZNLHJCCGYKCIL-UHFFFAOYSA-N 6-ethoxy-6-oxohexanoic acid Chemical compound CCOC(=O)CCCCC(O)=O UZNLHJCCGYKCIL-UHFFFAOYSA-N 0.000 abstract 1
- QGZPOYAPRDZVPK-UHFFFAOYSA-N Cl.C(CCCCCC(=O)O)(=O)NN Chemical compound Cl.C(CCCCCC(=O)O)(=O)NN QGZPOYAPRDZVPK-UHFFFAOYSA-N 0.000 abstract 1
- JUQLUIFNNFIIKC-YFKPBYRVSA-N L-2-aminopimelic acid Chemical compound OC(=O)[C@@H](N)CCCCC(O)=O JUQLUIFNNFIIKC-YFKPBYRVSA-N 0.000 abstract 1
- MGZWFYUWZLDZCJ-UHFFFAOYSA-N N-acetyl-N-(1,6-dihydrazinyl-1,6-dioxohexan-2-yl)acetamide Chemical compound C(C)(=O)N(C(CCCC(=O)NN)C(=O)NN)C(C)=O MGZWFYUWZLDZCJ-UHFFFAOYSA-N 0.000 abstract 1
- GUSWSMKTFRKUPI-UHFFFAOYSA-N N-acetyl-N-(1,7-dihydrazinyl-1,7-dioxoheptan-2-yl)acetamide Chemical compound C(C)(=O)N(C(CCCCC(=O)NN)C(=O)NN)C(C)=O GUSWSMKTFRKUPI-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HERPVHLYIHBEFW-ZETCQYMHSA-N diethyl (2s)-2-aminopentanedioate Chemical compound CCOC(=O)CC[C@H](N)C(=O)OCC HERPVHLYIHBEFW-ZETCQYMHSA-N 0.000 abstract 1
- USFFLCDBJZRSRV-UHFFFAOYSA-N diethyl 2-(diacetylamino)heptanedioate Chemical compound C(C)OC(CCCCC(C(=O)OCC)N(C(C)=O)C(C)=O)=O USFFLCDBJZRSRV-UHFFFAOYSA-N 0.000 abstract 1
- XLKHVETZXHBWLD-UHFFFAOYSA-N diethyl 2-acetamidoheptanedioate Chemical compound CCOC(=O)CCCCC(NC(C)=O)C(=O)OCC XLKHVETZXHBWLD-UHFFFAOYSA-N 0.000 abstract 1
- DHLXNZSKDRBWBE-UHFFFAOYSA-N dimethyl 2-(diacetylamino)hexanedioate Chemical compound COC(CCCC(C(=O)OC)N(C(C)=O)C(C)=O)=O DHLXNZSKDRBWBE-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 abstract 1
- UWNBKRSENSOXKX-UHFFFAOYSA-N ethyl 6-oxohexanoate Chemical compound CCOC(=O)CCCCC=O UWNBKRSENSOXKX-UHFFFAOYSA-N 0.000 abstract 1
- SQOMZPCAODNNSO-UHFFFAOYSA-N ethyl 7-oxoheptanoate Chemical compound CCOC(=O)CCCCCC=O SQOMZPCAODNNSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- LUFAVEPXCOBTOE-UHFFFAOYSA-N n-(1,7-dihydrazinyl-1,7-dioxoheptan-2-yl)acetamide Chemical compound CC(=O)NC(C(=O)NN)CCCCC(=O)NN LUFAVEPXCOBTOE-UHFFFAOYSA-N 0.000 abstract 1
- 235000011056 potassium acetate Nutrition 0.000 abstract 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0811780/IV (b)/1> (wherein R is -CH=NNHCSNH2 or R and R1 are jointly H2NCSNHN =, R2 being -H, -NH2 or -NHCOCH3 and R3 being -COOC2 H5; or R is -CONHNH2, R1 and R2 being -H, -NH2 or -NHCOCH3 and R3 being -COOH or -CONHNH2, and n is 1, 2 or 3, at least one of the groups R1 and R2 being -NH2 or -NHCOCH3 when R and R3 are both -CONHNH2), the preparation of the dihydrazides by heating the corresponding dimethyl or di-ethyl esters with excess of hydrazine hydrate, with or without alcohol solvent, the preparation of the monocarboxy mono-hydrazides by treating the corresponding mono-carboxy mono-(methyl or ethyl) esters with an excess of hydrazine hydrate in the cold, bringing the liquid to dryness and taking the residue up in acetone, and hydrolysing the mono-hydrazide isopropylidene derivative thus obtained with HCl in acetone-ether or ether solution, and the preparation of the thiosemicarbazones by reacting the corresponding aldehydes with an excess of thiosemicarbazide in water-alcohol solution. In examples: (1) monoethyl adipate is left to stand with excess hydrazine hydrate, the excess of hydrazine is removed, the mixture is refluxed with acetone to give adipic acid isopropylidene-mono-hydrazide and this is hydrolysed with HCl in ether to give adipic acid monohydrazide hydrochloride; (2) pimelic acid monohydrazide hydrochloride is similarly prepared; (3) L-glutamic acid diethyl ester is refluxed with hydrazine hydrate in ethanol to give L-glutamic acid dihydrazide; (4) 2 : 5-diamino-adipic acid dimethyl ester hydrochloride is refluxed with potassium acetate and acetic anhydride to give 2 : 5-diacetylamino-adipic acid dimethyl ester, which on refluxing with hydrazine hydrate in ethanol gives 2 : 5-diacetylamino-adipic acid dihydrazide; (5) 2 : 6-dibromopimelic acid diethyl ester is refluxed with potassium phthalimide in dimethyl formamide to give 2 : 6-diphthalimido-pimelic acid diethyl ester, this on hydrolysis with hydrazine hydrate and then HCl gives 2 : 6-diamino-pimelic acid hydrochloride (and, as a by-product which is removed, 1 : 4-dihydroxyphthalazine), this on refluxing with ethanol in presence of anhydrous HCl gives 2 : 6-diaminopimelic acid diethyl ester hydrochloride, this on acetylation with acetic anhydride and pyridine at 20 DEG C. gives 2 : 6-diacetylamino-pimelic acid diethyl ester, and this on refluxing with hydrazine hydrate in ethanol gives 2 : 6-diacetylamino pimelic acid dihydrazide; (6) 2-amino-pimelic acid is boiled with HCl-saturated ethanol, the product is reacted with acetic anhydride in pyridine to give 2-acetylamino-pimelic acid diethyl ester and this is converted to 2-acetylaminopimelic acid dihydrazide by the method of (3); (7) ethyl 6-formyl-caproate is refluxed with thiosemicarbazide in ethanol to give the thiosemicarbazone; and (8) the thiosemicarbazone of ethyl 5-formylvalerate is similarly prepared.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT811780X | 1954-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB811780A true GB811780A (en) | 1959-04-15 |
Family
ID=11317141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20288/55A Expired GB811780A (en) | 1954-07-16 | 1955-07-13 | Hydrazides and thiosemicarbazones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB811780A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2144742A (en) * | 1983-08-10 | 1985-03-13 | Nuclear Technology Corp | Hydrazides of amino-polyacetic acids as chelants |
-
1955
- 1955-07-13 GB GB20288/55A patent/GB811780A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2144742A (en) * | 1983-08-10 | 1985-03-13 | Nuclear Technology Corp | Hydrazides of amino-polyacetic acids as chelants |
| US4609757A (en) * | 1983-08-10 | 1986-09-02 | Nuclear Technology Corporation | Hydrazides of amino-polyacetic acids as chelants |
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