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

HRID 233679Notes

Reaction equation

HRID 233679 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-d1aa0f1a5ed244b98b66ba699e7fc273
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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