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

HRID 742249Notes

Reaction equation

HRID 742249 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[N:16]=[C:17]=[S:18].C(N(CC)CC)C>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[N:16]1[C:5](=[O:7])[CH2:4][N:3]([CH2:1][CH3:2])[C:17]1=[S:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 316542N-EthylglycineHCID 37317252-Chloro-6-Methylphenyl Isothiocyanate

Product 1

HCID 111615193-(2-Chloro-6-methylphenyl)-1-ethyl-2-thioxo-imidazolidin-4-oneYield 40.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the procedure described in Example 19 using 9.2 g of N-ethyl glycine, 9.1 g of 2-chloro-6-methylphenyl-isothiocyanate, 10.1 g of triethylamine, and 150 mL of methylene chloride. Purification was achieved by flash chromatography on silica gel (methylene chloride). Crystallization from ethanol afforded the title compound (5.4 g) as a creamy solid, m.p. 124°-126° C. Anal. Calcd. for. C12H13Cl N2O S: C, 53.63; H, 4.87; N, 10.42. Found: C, 53.43; H, 4.79; N, 10.28. Mass spectrum (El, M.+) m/z 268/270.

Workup

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

Sources & evidence

ORD record
ord-618207c689af4ebc989deabbccc6c31e
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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