Hydrochloric Acid → HCID 86722772、化合物

HRID 2203392

反応式

HRID 2203392 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.[Br:15][C:16]1[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][C:17]=1[CH:18]=O.[C:26]([O:32][CH3:33])(=[O:31])[CH2:27][C:28]([CH3:30])=O.C[Si](OP([O-])([O-])=O)(C)C.Cl>C1COCC1>[CH3:33][O:32][C:26]([C:27]1[CH:18]([C:17]2[CH:20]=[CH:21][C:22]([C:24]#[N:25])=[CH:23][C:16]=2[Br:15])[NH:12][C:10](=[S:11])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[C:28]=1[CH3:30])=[O:31]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 7358443-(Trifluoromethyl)phenylthioureaHCID 18172808TrimethylsilylphosphateHCID 205105183-Bromo-4-formylbenzonitrile

生成物 1

HCID 86722772HCID 86722772、化合物収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
75 °C

実験手順

3-Trifluoromethylphenylthiourea (12.8 g, 87 mmol), 2-bromo-4-cyanobenzaldehyde (18.3 g, 87 mmol), and methyl acetoacetate (10.4 mL, 96 mmol) were dissolved in THF (300 mL) under an atmosphere of N2 and then trimethylsilylphosphate (18 g) in THF (50 mL) was added, and the mixture heated at 75° C. After 17 hours the reaction mixture was allowed to cool, poured onto 0.5 M HCl (600 mL) and stirred for 30 minutes. The mixture was extracted into EtOAc. The organic phase was washed with water, then brine and dried (Na2SO4) before being concentrated in vacuo. The resulting solid was triturated with Et2O (50 mL), filtered and the solid collected to yield the title compound as a white solid (22.2 g).

後処理

  1. temperatureto cool
  2. extractionThe mixture was extracted into EtOAc
  3. washThe organic phase was washed with water
  4. dry with materialbrine and dried (Na2SO4)
  5. concentrationbefore being concentrated in vacuo
  6. customThe resulting solid was triturated with Et2O (50 mL)
  7. filtrationfiltered
  8. customthe solid collected

出典と根拠

ORDレコード
ord-af3de181f6d14fd1a0a3cbdb6e80e403
出典データセット
uspto-grants-2016_06
特許番号
US09365577B2

関連ノート

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