Triethylamine → 3-(2-Chloro-6-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-one

HRID 742235Notes

Reaction equation

HRID 742235 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]=[C:10]=[S:11].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][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:16](=[O:15])[CH2:17][N:18]([CH3:19])[C:10]1=[S:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 37317252-Chloro-6-Methylphenyl Isothiocyanate

Product 1

HCID 114253423-(2-Chloro-6-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-oneYield 55.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared by the procedure described in Example 1 using 9.2 g of 2-chloro-6-methylphenyl-isothiocyanate, 7.68 g of sarcosine ethyl ester hydrochloride, 12 g of triethyl amine, and 200 mL of chloroform. Crystallization from ethanol afforded the title compound (7.1 g) as an orange solid (7.1 g), m.p. 142°-145° C. Anal. Calcd. for. C11H11N2O S: C, 51.87; H, 4.35; N,11.00. Found: C, 51.96; H, 4.26; N, 10.97. Mass spectrum (El, M.+) m/z 254.

Workup

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

Sources & evidence

ORD record
ord-fac5c77daf104020a734746a13c2f567
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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