Pivaloyl chloride → 2-(4-Trimethylacetylthiophenyl)3-(4-pyridyl)-6,7-dihydro [5H]-pyrrolo[1,2 a]imidazole
Reaktionsgleichung
[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.[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25]>C(Cl)Cl>[CH3:22][C:23]([CH3:28])([CH3:27])[C:24]([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:25]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To 1.0 q (3.4 mmole) of 2-(4 mercaptophenyl)-3-(4-pyridyl)-6,7-dihydro [5H]pyrrolo[1,2-a]imidazole prepared as in Example 16 in 50ml methylene chloride at ° C. was added a solution of 0.3 q (3.7 mmole, 0.26 ml) trimethylacetyl 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 N 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 from ethyl acetate to give 0.43 g of the titled compound. 33.5% yield, mp 216-217.5 ° C. C22H23N3OS, Calculated, C: 70.00, H: 6.14, N: 1.13; Found, C: 70.01, H: 6.20, N: 10.99.