2-Aminothiazole → Thiourea, N-ethyl-N'-2-thiazolyl-

HRID 2257758Notes

Reaction equation

HRID 2257758 reaction equation
[CH2:1]([N:3]=[C:4]=[S:5])[CH3:2].[NH2:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1)=[S:5])[CH3:2]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 8857Ethyl AcetateHCID 10966Ethyl isothiocyanate

Product 1

HCID 4762507Thiourea, N-ethyl-N'-2-thiazolyl-Yield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl isothiocyanate (1.74 g, 20 mmol) and 2-aminothiazole (2.0 g, 20 mmol) in N,N-dimethylformamide (50 mL) was heated at 100° C. for 23 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 0.48 g (13%) 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-4fd4789e1ea449ba8f4f1e20a0781ce4
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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