GB812256A - A carbamic acid ester having a sedative effect and methods for the preparation thereof - Google Patents
A carbamic acid ester having a sedative effect and methods for the preparation thereofInfo
- Publication number
- GB812256A GB812256A GB3059657A GB3059657A GB812256A GB 812256 A GB812256 A GB 812256A GB 3059657 A GB3059657 A GB 3059657A GB 3059657 A GB3059657 A GB 3059657A GB 812256 A GB812256 A GB 812256A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbinol
- reacting
- urea
- preparation
- acid ester
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title abstract 2
- 230000001624 sedative Effects 0.000 title 1
- -1 alkali metal cyanates Chemical class 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- MERFIXJZPPDQCU-UHFFFAOYSA-N (2-methyl-1-phenylpropyl) carbamate Chemical compound NC(=O)OC(C(C)C)C1=CC=CC=C1 MERFIXJZPPDQCU-UHFFFAOYSA-N 0.000 abstract 1
- GMDYDZMQHRTHJA-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-ol Chemical compound CC(C)C(O)C1=CC=CC=C1 GMDYDZMQHRTHJA-UHFFFAOYSA-N 0.000 abstract 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N 420-05-3 Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960004319 Trichloroacetic Acid Drugs 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N Trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L Zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 230000001264 neutralization Effects 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- VYWQTJWGWLKBQA-UHFFFAOYSA-M urea;chloride Chemical compound [Cl-].NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-M 0.000 abstract 1
- 150000003672 ureas Chemical class 0.000 abstract 1
- 150000003673 urethanes Chemical class 0.000 abstract 1
- 239000004246 zinc acetate Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Abstract
The invention comprises phenyl-isopropyl-methyl carbamate and the preparation thereof by the following methods: (1) reacting phenyl-isopropyl-carbinol with cyanic acid, e.g. by heating with alkali metal cyanates in neutral solvents such as methylene chloride in the presence of acids such as trichloracetic acid; (2) reacting the carbinol at low temperatures with urea chloride or at elevated temperatures with urea, with or without the addition of heavy metal salts, e.g. zinc acetate, or with urea salts; (3) reacting the carbinol with urethanes such as ethyl urethane, with or without the addition of reaction accelerators such as sodium alcoholate, by heating; or (4) converting the carbinol to the chlorocarbonic acid ester thereof by means of phosgene, e.g. in a solvent such as toluene, and then reacting this ester with ammonia. Examples are given.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB812256A true GB812256A (en) | 1959-04-22 |
Family
ID=1742151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3059657A Expired GB812256A (en) | 1957-09-30 | A carbamic acid ester having a sedative effect and methods for the preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB812256A (en) |
-
1957
- 1957-09-30 GB GB3059657A patent/GB812256A/en not_active Expired
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