Acetyl chloride → 1-Acetyl-2-{[[4-(2-furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}benzimidazole

HRID 1871944Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[C:9]=1[CH3:25].C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34]>C(Cl)Cl>[C:33]([N:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=[C:16]1[S:15][CH2:14][C:10]1[C:9]([CH3:25])=[C:8]([S:7][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][N:11]=1)(=[O:35])[CH3:34]

Participants

Conditions

Temperature: 20 °C

Procedure

2-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazole (5.0 mmol) is suspended in anhydrous methylene chloride (50 ml), triethylamine (11 mmol and acetyl chloride (8 mmol) are added and the mixture is stirred at 20° C. for 20 h. The clear reaction solution is washed with sodium bicarbonate solution and water, dried over magnesium sulfate and concentrated and the residue is crystallized by addition of diisopropyl ether. The title compound is obtained as a colorless powder; m.p. 168-169° C. (decomp.); yield: 97% of theory.

Workup

washThe clear reaction solution is washed with sodium bicarbonate solution and water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customthe residue is crystallized by addition of diisopropyl ether

Sources & evidence

ORD record: ord-e8aa1f19f88a449eb8209ee9a52528c0
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107312

Reaction notes

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