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

HRID 359714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359714
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 545225782-(4-Acetylthiophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazoleAusbeute 17,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4d97924490244eed823b2cb32aabe496
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05002941

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