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

HRID 250001Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To 1H-benzo[d]imidazol-2-amine (1.28 g, 9.61 mmol) in acetonitrile (30 mL) was added 1,1′-thiocarbonyldiimidazole (2.227 g, 12.5 mmol). The reaction mixture 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—(1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide (1.8 g, 7.4 mmol, 77% 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-857a1ed9da654a39863a890504579c2b
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863291B2

Reaction notes

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