2-Amino-4-methylbenzothiazole → N-(4-methylbenzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide

HRID 249999

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To 4-methylbenzo[d]thiazol-2-amine (1.1 g, 6.7 mmol) in acetonitrile (30 mL) was added 1,1′-thiocarbonyldiimidazole (1.552 g, 8.71 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 (50° C.) for 1 hour to yield N-(4-methylbenzo[d]thiazol-2-yl)-1H-imidazole-1-carbothioamide (900 mg, 3.28 mmol, 49% 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 (50° C.) for 1 hour

Sources & evidence

ORD record: ord-c961a56e920f41b98c09e6183cab8541
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863291B2

Linked notes

Loading…