1H-Benzotriazole-1-carboxaldehyde → HCID 86617531、化合物

HRID 554097ノート

反応式

HRID 554097 の反応式
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH2:13].[CH:14](N1C2C=CC=CC=2N=N1)=[O:15]>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][CH:14]=[O:15]

参加物

4

反応物 2

HCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 52242072-Chloro-3-(trifluoromethyl)benzylamine

生成物 1

HCID 86617531HCID 86617531、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
22 °C

実験手順

A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (1.05 g, 5 mmol) in anhydrous tetrahydrofuran (10 ml) was added dropwise to a solution of N-formyl benzotriazole (0.772 g, 5.25 mmol) in anhydrous tetrahydrofuran (10 ml). The reaction was stirred at 22° C. for 18 hrs then reduced in vacuo and the residue partitioned between dichloromethane (75 ml) and 2N aqueous sodium hydroxide (40 ml). The organic layer was separated and extracted with 2N aqueous sodium hydroxide (40 ml). The organic layer was passed through a hydrophobic frit and reduced in vacuo to give a white solid. The crude product was purified by automated flash silica column chromatography (Biotage SP4), eluting with a solvent gradient of 0-10% ethyl acetate in dichloromethane, to give {[2-chloro-3-(trifluoromethyl)phenyl]methyl}formamide as a white solid.

後処理

  1. customthe residue partitioned between dichloromethane (75 ml) and 2N aqueous sodium hydroxide (40 ml)
  2. customThe organic layer was separated
  3. extractionextracted with 2N aqueous sodium hydroxide (40 ml)
  4. customto give a white solid
  5. customThe crude product was purified by automated flash silica column chromatography (Biotage SP4)
  6. washeluting with a solvent gradient of 0-10% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-b3be5526566349b28bd9d43bbc96de7f
出典データセット
uspto-grants-2011_11
特許番号
US08048907B2

反応ノート

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