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

HRID 359714ノート

反応式

HRID 359714 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4d97924490244eed823b2cb32aabe496
出典データセット
uspto-grants-1991_03
特許番号
US05002941

反応ノート

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