GB1068650A - Novel propane-carbamates,processes for preparing them,and compositions containing them - Google Patents
Novel propane-carbamates,processes for preparing them,and compositions containing themInfo
- Publication number
- GB1068650A GB1068650A GB54300/65A GB5430065A GB1068650A GB 1068650 A GB1068650 A GB 1068650A GB 54300/65 A GB54300/65 A GB 54300/65A GB 5430065 A GB5430065 A GB 5430065A GB 1068650 A GB1068650 A GB 1068650A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propyl
- methyl
- diol
- chlorophenylpropane
- acyloxy
- 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
- 239000000203 mixture Substances 0.000 title abstract 2
- KNXFNHQNBPBCMT-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-methyl-2-propylbutane-1,3-diol Chemical compound CC(CO)(C(O)(C1=CC=C(C=C1)Cl)C)CCC KNXFNHQNBPBCMT-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- -1 compound 2,3 - dimethyl - 2 - n - propyl - 3 - p -chlorophenylpropane - 1,3 - diol - 1 - monocarbamate Chemical class 0.000 abstract 2
- METJRNPZJAUAGA-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpentanoic acid Chemical compound CCCC(C)(CO)C(O)=O METJRNPZJAUAGA-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- JVZZUPJFERSVRN-UHFFFAOYSA-N 2-methyl-2-propylpropane-1,3-diol Chemical compound CCCC(C)(CO)CO JVZZUPJFERSVRN-UHFFFAOYSA-N 0.000 abstract 1
- NZUGGMISMNJLGR-UHFFFAOYSA-N 3-(hydroxymethyl)-3-methylhexan-2-one Chemical compound CC(C(C)=O)(CO)CCC NZUGGMISMNJLGR-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 208000010513 Stupor Diseases 0.000 abstract 1
- RFDUXXYHBPKLBS-UHFFFAOYSA-N [2-[1-(4-chlorophenyl)-1-hydroxyethyl]-1-hydroxy-2-methylpentyl]carbamic acid Chemical compound CCCC(C)(C(NC(=O)O)O)C(C)(C1=CC=C(C=C1)Cl)O RFDUXXYHBPKLBS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229940125717 barbiturate Drugs 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises the novel compound 2,3 - dimethyl - 2 - n - propyl - 3 - p -chlorophenylpropane - 1,3 - diol - 1 - monocarbamate and its diastereoisomeric forms, and the preparation thereof by reacting 2,3-dimethyl-2-n - propyl - 3 - p - chlorophenylpropane - 1,3-diol with phosgene, then ammonia. The 2,3 - dimethyl - 2 - n - propyl - 3 - p-chlorophenylpropane-1,3-diol may be prepared by reacting 2-methyl-2-n-propylpropane-1,3-diol with an oxidizing agent in an alkaline medium acylating the 2-methyl-2-n-propyl-3-hydroxypropionic acid formed, and reacting the 3 - acyloxy - 2 - methyl - 2 - n - propylpropionic acid thus produced with a chlorinating agent to give the 3-acyloxy-2-methyl-2-n-propylpropionic acid chloride which is then converted to the 4-acyloxy - 3 - methyl - 3 - n - propyl - 2 - butanone by reaction with a methyl metallic halide, the 4 - acyloxy - 3 - methyl - 3 - n - propyl - 2-butanone is then reacted with an alkali metal hydroxide to give 3-methyl-3-n-propyl-4-hydroxy-2-butanone which is converted to the desired product by reaction with p-chlorophenylmagnesium halide. Therapeutic compositions, having tranquilizing activity and a marked potentiating effect on narcosis caused by barbiturates, which may be administered, e.g. orally, rectally or by injection, contain as active ingredient 2,3-dimethyl-2 - n - propyl - 3 - p - chlorophenylpropane-1,3-diol-1-monocarbamat or its diastereoisomeric forms.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR999590A FR4475M (en) | 1964-12-22 | 1964-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1068650A true GB1068650A (en) | 1967-05-10 |
Family
ID=8845349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB54300/65A Expired GB1068650A (en) | 1964-12-22 | 1965-12-22 | Novel propane-carbamates,processes for preparing them,and compositions containing them |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE673250A (en) |
| CH (1) | CH448990A (en) |
| DE (1) | DE1294953B (en) |
| FR (1) | FR4475M (en) |
| GB (1) | GB1068650A (en) |
| NL (1) | NL145848B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0082344A1 (en) * | 1981-12-11 | 1983-06-29 | American Hoechst Corporation | Process for preparing beta-hydroxy-beta-methylglutaric acid |
| US4546203A (en) * | 1981-12-11 | 1985-10-08 | American Hoechst Corporation | Facile synthesis of β-hydroxy-β-methylglutaric acid |
| WO2004041948A1 (en) * | 2002-10-31 | 2004-05-21 | Basf Corporation | Compounds having a secondary or tertiary hydroxy or halide group separated from a primary carbamate group by three or more carbon atoms and a method of making the same |
| US6858674B2 (en) * | 2002-10-31 | 2005-02-22 | Basf Corporation | Carbamate functional materials, a method of making said materials, and curable coating compositions containing said materials |
| US6890994B2 (en) | 2002-10-31 | 2005-05-10 | Basf Corporation | Curable coating compositions with carbamate-containing acrylic polymers |
| US6900270B2 (en) | 2002-10-31 | 2005-05-31 | Basf Corporation | Curable coating compositions with carbamate compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1063146B (en) * | 1957-08-16 | 1959-08-13 | Hoffmann La Roche | Process for the production of carbamic acid esters |
-
1964
- 1964-12-22 FR FR999590A patent/FR4475M/fr not_active Expired
-
1965
- 1965-12-03 BE BE673250D patent/BE673250A/xx unknown
- 1965-12-07 DE DE1965R0042156 patent/DE1294953B/en active Pending
- 1965-12-07 NL NL656515912A patent/NL145848B/en unknown
- 1965-12-21 CH CH1756265A patent/CH448990A/en unknown
- 1965-12-22 GB GB54300/65A patent/GB1068650A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0082344A1 (en) * | 1981-12-11 | 1983-06-29 | American Hoechst Corporation | Process for preparing beta-hydroxy-beta-methylglutaric acid |
| US4546203A (en) * | 1981-12-11 | 1985-10-08 | American Hoechst Corporation | Facile synthesis of β-hydroxy-β-methylglutaric acid |
| WO2004041948A1 (en) * | 2002-10-31 | 2004-05-21 | Basf Corporation | Compounds having a secondary or tertiary hydroxy or halide group separated from a primary carbamate group by three or more carbon atoms and a method of making the same |
| US6858674B2 (en) * | 2002-10-31 | 2005-02-22 | Basf Corporation | Carbamate functional materials, a method of making said materials, and curable coating compositions containing said materials |
| US6890994B2 (en) | 2002-10-31 | 2005-05-10 | Basf Corporation | Curable coating compositions with carbamate-containing acrylic polymers |
| US6900270B2 (en) | 2002-10-31 | 2005-05-31 | Basf Corporation | Curable coating compositions with carbamate compounds |
| US6977309B2 (en) | 2002-10-31 | 2005-12-20 | Basf Corporation | Compounds having a secondary or tertiary hydroxy of halide group separated from a primary carbamate group by three or more carbon atoms and a method of making the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CH448990A (en) | 1967-12-31 |
| NL145848B (en) | 1975-05-15 |
| DE1294953B (en) | 1969-05-14 |
| FR4475M (en) | 1966-10-03 |
| NL6515912A (en) | 1966-06-23 |
| BE673250A (en) | 1966-06-03 |
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