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GB1068650A - Novel propane-carbamates,processes for preparing them,and compositions containing them - Google Patents

Novel propane-carbamates,processes for preparing them,and compositions containing them

Info

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
Application number
GB54300/65A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1068650A publication Critical patent/GB1068650A/en
Expired legal-status Critical Current

Links

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)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (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.
GB54300/65A 1964-12-22 1965-12-22 Novel propane-carbamates,processes for preparing them,and compositions containing them Expired GB1068650A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (7)

* Cited by examiner, † Cited by third party
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
NL145848B (en) 1975-05-15
BE673250A (en) 1966-06-03
NL6515912A (en) 1966-06-23
DE1294953B (en) 1969-05-14
CH448990A (en) 1967-12-31
FR4475M (en) 1966-10-03

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