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

HRID 399596

Reaction equation

HRID 399596 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([N:8]=[C:9]=[S:10])[CH:5]=[CH:6][CH:7]=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[C:3]([CH3:11])=[C:4]([N:8]2[C:16](=[O:15])[CH2:17][N:18]([CH3:19])[C:9]2=[S:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1405041-Chloro-3-isothiocyanato-2-methylbenzeneHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 189682123-(3-Chloro-2-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-oneYield 83.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared by the procedure described in Example 1 using 13.2 g of 3-chloro-2-methylphenyl-isothiocyanate, 11.0 g of sarcosine ethyl ester hydrochloride, 25 g of triethyl amine, and 300 mL of chloroform. Crystallization from diethyl ether afforded the title compound (15.2 g) as a tan solid, m.p. 122°-124° C. Anal. Calcd. for C11H11Cl N2O S: C, 51.87; H, 4.35; N,11.00. Found: C, 51.96; H, 4.21; N, 11.05. Mass spectrum (EI, 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-58317836117e413f82d1d06fa2f3cd8b
Source dataset
uspto-grants-1998_10
Patent number
US05821372

Linked notes

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