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

HRID 861575Notes

Reaction equation

HRID 861575 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-6b89eff6b64944cb966284671db2e0d1
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

Loading…