Methyl iodide → HCID 178504145, compound

HRID 1089245Notes

Reaction equation

[C:1]([NH:9][C:10]([NH:12][C:13]1[N:17]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:16]=[N:15][C:14]=1[C:30]([NH2:32])=[O:31])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:35]I>C(O)(=O)C>[C:1]([NH:9][C:10]([NH:12][C:13]1[N:17]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:16]=[N:15][C:14]=1[C:30]([NH2:32])=[O:31])=[SH:11][CH3:35])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 5-(N'-benzoylthiocarbamoyl)amino-1-(3-benzyloxyprop-1-oxy)imidazole-4-carboxamide (2.9 g, 6.4 mmol), 0.1N sodium hydroxide solution (100 ml) and methyl iodide (0.64 ml; 10.3 mmol) was stirred at 20° C. for 16 hours and then the solution adjusted to pH 5 with glacial acetic acid. After several extractions with chloroform, the combined extracts were dried (magnesium sulphate) and evaporated to a syrup. Column chromatography on silica gel (eluted with chloroformethanol, 30:1) afforded the title compound (2.7 g, 88.7%).

Workup

extractionAfter several extractions with chloroform
dry with materialthe combined extracts were dried (magnesium sulphate)
customevaporated to a syrup

Sources & evidence

ORD record: ord-b36dda11cf6248e1802e6641962e4bc5
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965270

Reaction notes

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