2-Aminothiazole → N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide

HRID 1875873Notes

Reaction equation

HRID 1875873 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].[N:7]1([C:12](N2C=CN=C2)=[S:13])[CH:11]=[CH:10][N:9]=[CH:8]1>C(#N)C.O1CCCC1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:12]([N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)=[S:13]

Participants

5

Reactant 2

HCID 21552-AminothiazoleHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 10750950N-(thiazol-2-yl)-1H-imidazole-1-carbothioamideYield 83.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To thiazol-2-amine (2.12 g, 21.17 mmol) in acetonitrile (30 mL) and tetrahydrofuran (5 mL) was added di(1H-imidazol-1-yl)methanethione (4.90 g, 27.5 mmol). The reaction was stirred at 60° C. for 5 hours. The reaction was cooled to room temperature and the precipitate was filtered and washed with cold acetonitrile (2×15 mL) to afford an orange-brown powder. The product, N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide (3.70 g, 17.60 mmol, 83% yield), was taken directly to the next step without any further characterization.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe precipitate was filtered
  3. washwashed with cold acetonitrile (2×15 mL)
  4. customto afford an orange-brown powder

Sources & evidence

ORD record
ord-aaddb676184541509234f6b1acb5d3a0
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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