2-Aminothiazole → 1-Benzyl-3-thiazol-2-yl-thiourea

HRID 861576Notes

Reaction equation

HRID 861576 reaction equation
[CH2:1]([N:8]=[C:9]=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][C:12]1[S:13][CH:14]=[CH:15][N:16]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:1]([NH:8][C:9]([NH:11][C:12]1[S:13][CH:14]=[CH:15][N:16]=1)=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 2346Benzyl IsothiocyanateHCID 8857Ethyl Acetate

Product 1

HCID 7007231-Benzyl-3-thiazol-2-yl-thioureaYield 46.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of benzyl isothiocyanate (1.5 g, 10 mmol) and 2-aminothiazole (1.0 g, 10 mmol) in N,N-dimethylformamide. (25 mL) was heated at 100° C. for 12 h. The reaction was cooled to room temperature, poured into ethyl acetate, washed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine. The organic layer was concentrated and the residue recrystallized twice from ethyl acetate to provide 1.15 g (46%) of the title product:

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-adbb4c2a1d7143f2a14b6abe1159c8ab
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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