Triethylamine → 1-Ethyl-3-(2-ethylphenyl)-2-thioxo-imidazolidin-4-one

HRID 343610

Reaction equation

HRID 343610 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]=[C:10]=[S:11])[CH3:2].[CH2:12]([NH:14][CH2:15][C:16](O)=[O:17])[CH3:13].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:12]([N:14]1[CH2:15][C:16](=[O:17])[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:1][CH3:2])[C:10]1=[S:11])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 316542N-EthylglycineHCID 27962132-Ethylphenyl isothiocyanate

Product 1

HCID 98378041-Ethyl-3-(2-ethylphenyl)-2-thioxo-imidazolidin-4-oneYield 36.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared by the procedure described in Example 9 using 16.3 g of 2-ethylphenyl-isothiocyanate, 18.4 g of N-ethyl glycine, 20.2 g of triethyl amine, and 200 mL of chloroform. Purification was achieved by flash chromatography on silica gel (5-10% ethyl acetate in hexane). Crystallization from diethyl ether afforded the title compound (9.12 g) as a white solid, m.p. 71°-73° C. Anal. Calcd. for. C13H16N2OS: C, 62.87; H, 6.49; N, 11.28. Found: C, 62.81; H, 6.43; N, 11.17. Mass spectrum (EI, M.+) m/z 248.

Workup

  1. customThe title compound was prepared by the procedure
  2. customPurification
  3. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-a4c9b9fcac2f49c69c81434d510fc27e
Source dataset
uspto-grants-1999_01
Patent number
US05861517

Linked notes

Loading…