Hydrochloric Acid → 2-Chloro-3-(2-methyl-3-trifluoromethylphenyl)-propionitrile

HRID 374263

반응식

HRID 374263 반응식
[ClH:1].[CH3:2][C:3]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:4]=1N.[C:14](#[N:17])[CH:15]=[CH2:16].N([O-])=O.[Na+]>O.[Cu]=O.ClCCl>[Cl:1][CH:15]([CH2:16][C:4]1[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[C:3]=1[CH3:2])[C:14]#[N:17]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 2735932Trifluoromethyl toluidineHCID 23668193Sodium Nitrite

생성물 1

HCID 198096422-Chloro-3-(2-methyl-3-trifluoromethylphenyl)-propionitrile수율 90.1%

시약·촉매·용매 3

HCID 14829Copper oxide촉매HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

20 mol of concentrated hydrochloric acid is added at 0°-5° C. to a suspension of 16.7 g of 2-methyl-3-trifluoromethylaniline (0.095 mol) in 50 ml mixture is then briefly warmed to 60°-80° C. until a clear solution has formed. The solution is cooled very rapidly to 0°-5° C. with vigorous stirring, 22.4 ml (0.286 mol) of acrylonitrile are added dropwise to the fine suspension at 0°-5° C. and a solution of 6.75 g of sodium nitrite in 10 ml of water is then rapidly added, and the mixture is kept at 5° C. for a further 5 minutes and stirred at 20° C for 1 hour. After cooling, 0.8 g of copper(II) oxide powder is added to the reaction mixture at 0°-10° C. in portions, a vigorous evolution of nitrogen gas occurring. After completion of the evolution of gas, the mixture is stirred for a further 2 hours at 0°-10° C., then for 15 hours at room temperature, dichloromethane is added, and the mixture is washed with water, dried over sodium sulphate and concentrated in vacuo. 21.2 g (90% of theory) of 2-chloro-3-(2-methyl-3-trifluoromethylphenyl)-propionitrile are obtained as a brown oil. M/e 247 (M+), 228, 212, 173 (100%)

후처리

  1. temperatureis then briefly warmed to 60°-80° C. until a clear solution
  2. customhas formed
  3. additionare added dropwise to the fine suspension at 0°-5° C.
  4. temperatureAfter cooling
  5. stirringAfter completion of the evolution of gas, the mixture is stirred for a further 2 hours at 0°-10° C.
  6. waitfor 15 hours at room temperature
  7. washthe mixture is washed with water
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4c9fd72cd36149eb9b0bb8a9aec43639
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166395

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