Acetyl chloride → 2-(4-Acetylthiophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole

HRID 359714노트

반응식

HRID 359714 반응식
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1)(=[O:24])[CH3:23]

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 135962046(4-mercaptophenyl) 3 (4-pyridyl) 6,7dihydro[5H]-pyrrolo[1,2-a]imidazole

생성물 1

HCID 545225782-(4-Acetylthiophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole수율 17.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To 1.0 q (3.4 mmole) of 2-(4 mercaptophenyl)-(4 pyridyl)-6,7-dihydro [5H]-pyrrolo[1,2-a]imidazole prepared as in Example 16 in 50 ml methylene chloride at 0° C. was added a solution of 0.3 g (3.7 mmole, 0.26 ml) acetyl chloride in 10 ml CH2Cl2 over a period of 10 minutes. The reaction was allowed to come to room temperature and was stirred for 30 minutes. The mixture was then diluted with methylene chloride and washed with 3N NaHCO3, saturated NaCl, treated with Na2SO4, stripped, then flash chromatographed on silica with methylene chloride containing 1% to 5% MeOH. The isolated material was recrystallized twice from ethyl acetate to give 0.20 g of the titled compound. 17.6% yield, mp 216-217.5 152°-154° C. C19H17N3OS, Calculated, C: 68.03, H: 5.11, N: 12.53; Found, C: 68.25, H: 5.40, N: 12.14.

후처리

  1. customto come to room temperature
  2. washwashed with 3N NaHCO3, saturated NaCl
  3. additiontreated with Na2SO4
  4. customflash chromatographed on silica with methylene chloride containing 1% to 5% MeOH
  5. customThe isolated material was recrystallized twice from ethyl acetate

출처 및 근거

ORD 기록
ord-4d97924490244eed823b2cb32aabe496
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05002941

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