3-(Trifluoromethyl)benzoyl chloride → N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 77696

反応式

HRID 77696 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)C(C)C)(C)C.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25]>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([C:20]([F:19])([F:30])[F:31])[CH:22]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

参加物

5

反応物 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 1188893-Iodo-p-toluidine

生成物 1

HCID 7925506N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To 3-iodo-4-methylaniline (500.0 mg, 2.145 mmol) was added dichloromethane (DCM) (10 mL) followed by N,N-diisopropylethylamine (DIPEA)(520 μL, 3.0 mmol) and 3-(trifluoromethyl)-benzoyl chloride (0.36 mL, 2.4 mmol). The reaction was stirred at 25° C. for 16 hours and was transferred to a separatory funnel and partitioned between water and dichloromethane (DCM). The organic phase was sequentially washed with 0.1N HCl, saturated aqueous NaHCO3, water, then saturated aqueous NaCl. The washed organic phase was then dried over MgSO4 and filtered and concentrated to leave the crude product. The crude product was triturated with hexanes to leave the product as an off-white solid, (797 mg, 92%). 1H NMR (400 MHz, CDCl3): δ 8.10 (m, 2H), 8.04 (d, 1H), 7.84 (bs, 1H), 7.81 (d, 1H), 7.63 (m, 1H), 7.58 (dd, 1H), 7.22 (d, 1H), 2.42 (s, 3H). MS (EI) m/z=274 (M+H).

後処理

  1. customwas transferred to a separatory funnel
  2. custompartitioned between water and dichloromethane (DCM)
  3. washThe organic phase was sequentially washed with 0.1N HCl, saturated aqueous NaHCO3, water
  4. dry with materialThe washed organic phase was then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto leave the crude product
  8. customThe crude product was triturated with hexanes

出典と根拠

ORDレコード
ord-8e1d154a8b984a23affefa947ae0cdfe
出典データセット
uspto-grants-2014_09
特許番号
US08841318B2

関連ノート

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