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

HRID 233678Notes

Reaction equation

HRID 233678 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-435d4aee292a4e1ca4a831d9aa1af3e9
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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