1-Bromo-4-(chloro(isocyanato)methyl)benzene → HCID 86732297、化合物

HRID 517176ノート

反応式

HRID 517176 の反応式
[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

参加物

4

反応物 2

HCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzene2 回HCID 867322966,6-Dimethyl-3-(3-(trifluoromethyl)phenylamino)cyclohex-2-enone2 回

生成物 1

HCID 86732297HCID 86732297、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9332af675c264582a9133f172a674dd3
出典データセット
uspto-grants-2015_08
特許番号
US09115093B2

反応ノート

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