Triethylamine → 3-fluoro-N-(3-iodo-4-methylphenyl)-5-(trifluoromethyl)benzamide

HRID 1894872ノート

反応式

HRID 1894872 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].C(N(CC)CC)C.[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:21](Cl)=[O:22]>C(Cl)Cl>[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:26]=1)[C:21]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([I:1])[CH:3]=1)=[O:22]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1188893-Iodo-p-toluidineHCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chloride

生成物 1

HCID 690440933-fluoro-N-(3-iodo-4-methylphenyl)-5-(trifluoromethyl)benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

3-Iodo-4-methylaniline (2.42 g, 10.4 mmol) was dissolved in DCM (20.00 mL) and triethylamine (TEA) (1.70 mL, 12.2 mmol) was added and the resulting mixture was cooled to 0° C. To the mixture was added dropwise 3-fluoro-5-(trifluoromethyl)benzoyl chloride (1.60 mL, 10.5 mmol) and the resulting mixture was stirred at 0° C. for 45 minutes and at 25° C. for 16 hours. The reaction was extracted with ethyl acetate and the organic extracts were washed with water sat. Na2CO3, saturated NaCl, dried (MgSO4) and concentrated in vacuo. The reaction product was used in the next reaction without purification. 1H NMR (CDCl3): 8.98 (d, 1H), 7.78 (s, 1H), 7.72 (m, 2H), 7.55 (m, 2H), 7.23 (d, 1H), 2.42 (s, 3H). MS (EI) m/z=424 (M+H).

後処理

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe organic extracts were washed with water sat. Na2CO3, saturated NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe reaction product was used in the next reaction without purification

出典と根拠

ORDレコード
ord-561b80bc246f492ba433c6fb9972c322
出典データセット
uspto-grants-2013_08
特許番号
US08513270B2

反応ノート

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