GB1194081A - Substituted Phenylphosphonamides and their Production - Google Patents
Substituted Phenylphosphonamides and their ProductionInfo
- Publication number
- GB1194081A GB1194081A GB453268A GB453268A GB1194081A GB 1194081 A GB1194081 A GB 1194081A GB 453268 A GB453268 A GB 453268A GB 453268 A GB453268 A GB 453268A GB 1194081 A GB1194081 A GB 1194081A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- prepared
- alkali metal
- compounds
- reacting
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4419—Amides of aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65848—Cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,194,081. Nuclearly - substituted phenylphosphonamides. MERCK & CO. Inc. 29 Jan., 1968 [31 Jan., 1967], No. 4532/68. Heading C2C. The invention comprises compounds of general formula in which R 1 and R 2 are H or halogen; R 3 is H and may also be F when both R 1 and R 2 are H; Q is -O- or -NH-; R 4 is H, C 1 -C 5 alkyl, substituted phenyl, phenyl, C 1 -C 5 aminoalkyl, amino-phenyl, or (heterocyclosulphamoyl)-phenyl or an alkali metal salt thereof; and Z is H, C 1 -C 5 alkyl, or (heterocyclosulphamoyl)-phenyl or alkali metal salt thereof, or QZ is an -O-(alkali metal) group, or the group -P(NHR 4 )(QZ) is 2-H- 1,3,2-benzodiazaphosphole. They are prepared by reduction of the corresponding nitrobenzenephosphonamides, e.g. by hydrogenation in the presence of a catalyst such as palladium, platinum oxide or Raney nickel. The invention also comprises the following processes for the preparation of nitrobenzenephosphonamides corresponding to the amino compounds of Formula (I); (a) nitro compounds in which QZ is also -NHR 4 are prepared by reacting the corresponding phosphonic dihalide with an amine, followed by treatment with water; (b) nitro compounds in which QZ is OM, M being an alkali metal, are prepared by reacting a compound produced by process (a) with one equivalent of aqueous alkali metal base of formula MOH; (c) nitro compounds in which R 4 is 2- amino phenyl and QZ is OR 5 , R 5 being C 1 -C 5 alkyl, are prepared by reacting a compound produced by process (a) in which the P(NHR 4 ) 2 group is 2-H-1,3,2-benzodiazaphosphole, wth an alkanol of formula R 5 OH. Specified heterocyclic rings when R 4 and Z are (heterocyclosulphamoyl)-phenyl are pyrimidine, methyl and dimethylpyrimidine, thiazole, oxazole, dimethylisoxazole and quinoxaline. The compounds have bactericidal properties. In Example XIV, 2-fluoro-4-nitrobenzenephosphonyl dichloride is prepared by reacting 2-fluoro-4-nitrobenzene phosphonic acid with PCl 5 .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61280067A | 1967-01-31 | 1967-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1194081A true GB1194081A (en) | 1970-06-10 |
Family
ID=24454709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB453268A Expired GB1194081A (en) | 1967-01-31 | 1968-01-29 | Substituted Phenylphosphonamides and their Production |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH507307A (en) |
| DE (1) | DE1668467A1 (en) |
| FR (1) | FR1573919A (en) |
| GB (1) | GB1194081A (en) |
| NL (1) | NL6800803A (en) |
-
1968
- 1968-01-18 NL NL6800803A patent/NL6800803A/xx unknown
- 1968-01-26 CH CH123768A patent/CH507307A/en not_active IP Right Cessation
- 1968-01-29 GB GB453268A patent/GB1194081A/en not_active Expired
- 1968-01-30 DE DE19681668467 patent/DE1668467A1/en active Pending
- 1968-01-31 FR FR1573919D patent/FR1573919A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH507307A (en) | 1971-05-15 |
| FR1573919A (en) | 1969-07-11 |
| NL6800803A (en) | 1968-08-01 |
| DE1668467A1 (en) | 1971-10-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |