Triethylsilane → N-[5-Chloro-4-(2-chloro-ethyl)-2-methyl-phenyl]-acetamide

HRID 2211907

반응식

HRID 2211907 반응식
[Cl:1][C:2]1[C:3]([C:13](=O)[CH2:14][Cl:15])=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([CH2:13][CH2:14][Cl:15])=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 21963317N-[5-Chloro-4-(2-chloro-acetyl)-2-methyl-phenyl]-acetamide

생성물 1

HCID 21963171N-[5-Chloro-4-(2-chloro-ethyl)-2-methyl-phenyl]-acetamide수율 88.2%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

반응 조건

온도
60 °C

실험 절차

To a solution of N-[5-Chloro-4-(2-chloro-acetyl)-2-methyl-phenyl]-acetamide (10 g, 38.44 mmol) in trifluoroacetic acid (100 mL) at <20° C. was added portionwise, triethylsilane (15.35 mL, 96.1 mmol). The reaction was heated to 60° C. and stirred overnight. The reaction was cooled to rt and poured over ice/H2O and stirred for 30 min as a grey precipitate formed. The precipitate was collected by filtration and dried in vacuo overnight to give desired product (8.35 g, 33.92 mmol). Yield=88%; MS (APCI): 246 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.05 (s, 1H), 6.93 (bs, 1H, NH), 3.69 (t, J=7.26 Hz, 2H), 3.10 (t, J=7.26 Hz, 2H), 2.20 (d, J=4.48 Hz, 3H).

후처리

  1. temperatureThe reaction was cooled to rt
  2. stirringstirred for 30 min as a grey precipitate
  3. customformed
  4. filtrationThe precipitate was collected by filtration
  5. customdried in vacuo overnight

출처 및 근거

ORD 기록
ord-731ee461f91146d2852063712cd16c60
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101886B2

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