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

HRID 2257757Notes

Reaction equation

HRID 2257757 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

Procedure

A solution of benzyl isothiocyanate (1.5 g, 10 mmol) and 2-aminothiazole (1.0 g, 10 mmol) in N,N-dimethyl-formamide (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. washwashed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine
  2. concentrationThe organic layer was concentrated
  3. customthe residue recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-71ef8c37ad704013bd2ec97cebb52c6f
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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