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

HRID 77696

반응식

HRID 77696 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8e1d154a8b984a23affefa947ae0cdfe
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841318B2

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