1,1'-Thiocarbonyldiimidazole → n-(4-Isopropylthiazol-2-yl)-1h-imidazole-1-carbothioamide

HRID 250006Notes

Reaction equation

HRID 250006 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([NH2:9])[S:7][CH:8]=1)([CH3:3])[CH3:2].[CH:10]1[N:14]=[CH:13][N:12]([C:15](N2C=NC=C2)=[S:16])[CH:11]=1>C(#N)C>[CH:1]([C:4]1[N:5]=[C:6]([NH:9][C:15]([N:12]2[CH:11]=[CH:10][N:14]=[CH:13]2)=[S:16])[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 70640774-(Propan-2-yl)-1,3-thiazol-2-amine

Product 1

HCID 58088138n-(4-Isopropylthiazol-2-yl)-1h-imidazole-1-carbothioamideYield 55.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 4-isopropylthiazol-2-amine (1.04 g, 7.31 mmol) in acetonitrile (30 mL) was added 1,1-thiocarbonyldiimidazole (1.7 g, 9.5 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 2 hours. The product, N-(4-isopropylthiazol-2-yl)-1H-imidazole-1-carbothioamide (1.02 g, 4.04 mmol, 55.3% yield), was taken directly to the next step without any further purification.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe precipitate was filtered
  3. washwashed with acetonitrile (2×50 mL)
  4. customThe yellow powder was dried in a vacuum oven (40° C.) for 2 hours

Sources & evidence

ORD record
ord-7f43e3bcf82c40889725f5e1fa0e04df
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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