2-Aminothiazole → N-(2-[1-cyclohexenyl]ethyl)-N'-[2-thiazolyl]thiourea

HRID 2257756Notes

Reaction equation

HRID 2257756 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]=[C:10]=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[NH2:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1.C(OCC)(=O)C>CN(C)C=O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 8857Ethyl AcetateHCID 27358811-(2-Isothiocyanatoethyl)cyclohex-1-ene

Product 1

HCID 3003028N-(2-[1-cyclohexenyl]ethyl)-N'-[2-thiazolyl]thioureaYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(1-cyclohexenyl) ethyl isothiocyanate (3.3 g, 20 mmol) and 2-aminothiazole (2.0 g, 20 mmol) in N,N-dimethylformamide (20 mL) was heated at 100° C. for 24 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 from ethyl acetate to provide 2.66 g (50%) 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 from ethyl acetate

Sources & evidence

ORD record
ord-1a716195046d4e999904ee8aade10bf8
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

Loading…