1-Bromo-4-(chloro(isocyanato)methyl)benzene → HCID 86732297, 화합물

HRID 517176노트

반응식

HRID 517176 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[N:9]=[C:10]=[O:11])=[CH:4][CH:3]=1.[CH3:13][C:14]1([CH3:32])[C:19](=[O:20])[CH:18]=[C:17]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:16][CH2:15]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:18]3[C:19](=[O:20])[C:14]([CH3:32])([CH3:13])[CH2:15][CH2:16][C:17]=3[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=3)[C:10](=[O:11])[NH:9]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzene2회HCID 867322966,6-Dimethyl-3-(3-(trifluoromethyl)phenylamino)cyclohex-2-enone2회

생성물 1

HCID 86732297HCID 86732297, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 1-bromo-4-(chloro(isocyanato)methyl)benzene (569 mg, 2.31 mmol) in dichloromethane (5 mL) is added to a solution of 6,6-dimethyl-3-(3-(trifluoromethyl)-phenylamino)cyclohex-2-enone (intermediate 6, 654 mg, 2.31 mmol) in dichloromethane (15 mL), and the resulting mixture is heated at reflux for 4 h and stirred at room temperature over night. Another portion of 1-bromo-4-(chloro(isocyanato)methyl)benzene (283 mg, 1.15 mmol) is added and the mixture is heated at reflux for 24 h. The mixture is cooled to room temperature and all volatiles are evaporated. The residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 90:10 to 60:40). Yield: 372 mg; ESI mass spectrum: [(79Br)-M+H]+=493, [(81Br)-M+H]+=495; Retention time HPLC: 1.37 min (Z005—001).

후처리

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 4 h
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 24 h
  5. temperatureThe mixture is cooled to room temperature
  6. customall volatiles are evaporated
  7. customThe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 90:10 to 60:40)
  8. custom1.37 min (Z005—001)

출처 및 근거

ORD 기록
ord-9332af675c264582a9133f172a674dd3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115093B2

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