2-Amino-1-methylbenzimidazole → N-(1-methyl-1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide

HRID 1875869Notes

Reaction equation

[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[NH2:11].[C:12](N1C=CN=C1)([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[S:13]>C(#N)C>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[NH:11][C:12]([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[S:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To 1-methyl-1H-benzo[d]imidazol-2-amine (1.28 g, 8.7 mmol) in acetonitrile (30 mL) was added 1,1′-thiocarbonyldiimidazole (2.015 g, 11.31 mmol). The reaction was stirred at 50° C. for 18 hours. The reaction was cooled to room temperature and the precipitate was filtered and washed with acetonitrile (2×50 mL). The yellow powder was dried in a vacuum oven (40° C.) for 1 hour to yield N-(1-methyl-1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide (1.6 g, 6.22 mmol, 71.5% yield) and then used in the next step without any further purification or characterization.

Workup

temperatureThe reaction was cooled to room temperature
filtrationthe precipitate was filtered
washwashed with acetonitrile (2×50 mL)
customThe yellow powder was dried in a vacuum oven (40° C.) for 1 hour

Sources & evidence

ORD record: ord-a39c91d4cca444b3ba72942b40683cf9
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309577B2

Reaction notes

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