Bromine → ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257348ノート

反応式

HRID 1257348 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH2:10][CH3:11])[CH:6]=[CH:7][CH:8]=1.BrBr.S([O-])([O-])(=O)=S.[Na+].[Na+].[NH2:24][C:25](=[S:37])[CH2:26][N:27]1[CH:31]=[C:30]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:29]=[N:28]1>C(OCC)C>[CH3:11][C:10]1[S:37][C:25]([CH2:26][N:27]2[CH:31]=[C:30]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:29]=[N:28]2)=[N:24][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=1

参加物

6

反応物 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 137064Propiophenone, 3'-(trifluoromethyl)HCID 58127901HCID 58127901、化合物

生成物 1

HCID 58127553ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate収率 35%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Under a nitrogen atmosphere, to a solution (10 mL) of 1-[3-(trifluoromethyl)phenyl]propan-1-one (1.0 g, 4.95 mmol) in diethyl ether was added bromine (0.15 mL, 5.94 mmol) at 0° C., and the mixture was stirred at room temperature overnight. An aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (4 mL), the compound (175 mg, 0.82 mmol) obtained in Example 1b was added and the mixture was heated under reflux for 3 hr. The reaction mixture was allowed to cool and the solvent was evaporated under reduced pressure. The obtained crude product was purified by recrystallization (ethyl acetate-hexane) to give the title compound (112 mg, 35%) as colorless crystals.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in ethanol (4 mL)
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 3 hr
  8. temperatureto cool
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by recrystallization (ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-23f680971d8c4adc9db211e8e3054a6b
出典データセット
uspto-grants-2013_06
特許番号
US08461348B2

反応ノート

読み込み中…