Triethylamine → 3-(4-Chloro-2-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-one

HRID 742230

Reaction equation

HRID 742230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[C:4]([CH3:11])[CH:3]=1.Cl.C([O:15][C:16](=O)[CH2:17][NH:18][CH3:19])C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:15])[CH2:17][N:18]([CH3:19])[C:9]2=[S:10])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900213-Chloro-6-isothiocyanatotolueneHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 189682103-(4-Chloro-2-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-oneYield 58.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared by the procedure described in Example 1 using 9.18 g of 4-chloro-2-methylphenyl-isothiocyanate, 7.68 g of sarcosine ethyl ester hydrochloride, 12.0 g of triethyl amine, and 300 mL of chloroform. Crystallization from diethyl ether afforded the title compound (7.5 g) as an off-white solid, m.p. 113°-115° C. Anal. Calcd. for C11H11Cl N2O S: C, 51.87; H, 4.35; N,11.00. Found: C, 51.72; H, 4.17; N, 10.88. Mass spectrum (El, M.+) m/z 254/256.

Workup

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

Sources & evidence

ORD record
ord-eef7ef530d104d5283788085c867fb32
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Linked notes

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