1,1'-Thiocarbonyldiimidazole → N-(6-(difluoromethoxy)benzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide

HRID 250014Notes

Reaction equation

[F:1][CH:2]([F:14])[O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=1.[C:15](N1C=CN=C1)([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=[S:16]>C(#N)C>[F:14][CH:2]([F:1])[O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH:11][C:15]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)=[S:16])[S:10][C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 6-(difluoromethoxy)benzo[d]thiazol-2-amine (0.5 g, 2.3 mmol) in acetonitrile (15 mL) was added 1,1′-thiocarbonyldiimidazole (0.49 g, 2.8 mmol). The reaction was stirred at 70° C. overnight. The reaction was cooled to room temperature and the precipitate was filtered to yield N-(6-(difluoromethoxy)benzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide (500 mg, 1.53 mmol, 66.3% yield) as a yellow solid.

Workup

temperatureThe reaction was cooled to room temperature
filtrationthe precipitate was filtered

Sources & evidence

ORD record: ord-a4e910216bcd4b75b1ffbe90d99bf848
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863291B2

Reaction notes

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