Dimethylformamide → 4-chloro-N,N-diethyl-2-(trifluoromethyl)benzamide

HRID 2100606ノート

反応式

HRID 2100606 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])=[O:8])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 65578Oxalyl chlorideHCID 27738564-Chloro-2-(trifluoromethyl)benzoic acid

生成物 1

HCID 690558204-chloro-N,N-diethyl-2-(trifluoromethyl)benzamide収率 51%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of 4-chloro-2-(trifluoromethyl)benzoic acid (18.1 g, 80 mmol) in 500 mL of methylene chloride was added oxalyl chloride (60 mL of a 2.0 M solution in methylene chloride, 120 mmol) followed by N,N-dimethylformamide (0.2 mL). The reaction was allowed to stir at ambient temperature for 18 h. The volatiles were removed in vacuo to afford the crude acid chloride intermediate. The residue was taken up in 500 mL of methylene chloride and then there was added diethylamine (16.5 mL, 160 mmol). The resulting solution was allowed to stir at ambient temperature for 2 h, and then the mixture was concentrated to an oil. The residue was purified (ISCO, 0-30% EtOAc/hexane, 45 min) to afford 11.4 g (51%) of the title compound as a pale yellow oil.

後処理

  1. customThe volatiles were removed in vacuo
  2. customto afford the crude acid chloride intermediate
  3. stirringto stir at ambient temperature for 2 h
  4. concentrationthe mixture was concentrated to an oil
  5. customThe residue was purified (ISCO, 0-30% EtOAc/hexane, 45 min)

出典と根拠

ORDレコード
ord-db3fbee541414173a688f18645dbddf3
出典データセット
uspto-grants-2009_08
特許番号
US07572805B2

反応ノート

読み込み中…