6-Chloro-2-benzothiazolamine → N-(6-chlorobenzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide

HRID 1875868Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To 6-chlorobenzo[d]thiazol-2-amine (1.14 g, 6.17 mmol) in acetonitrile (30 mL) was added 1,1′-thiocarbonyldiimidazole (1.43 g, 8 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-(6-chlorobenzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide (1.16 g, 3.9 mmol, 64% 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-11e4b15d007c457f94bca67f2f1cb7d4
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309577B2

Reaction notes

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