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

HRID 399599Notes

Reaction equation

HRID 399599 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

A mixture of the crude N-ethyl glycine (9.2 g), 2-chloro-6-methylphenyl-isothiocyanate (9.1 g), triethylamine (10.1 g), and methylene chloride (150 mL) was heated at reflux for 3.5 hours. The solvent was evaporated to dryness. 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 N2 O S: C, 53.63; H, 4.87; N, 10.42. Found: C, 53.43; H, 4.79; N, 10.28. Mass spectrum (EI, M.+) m/z 268/270.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. customThe solvent was evaporated to dryness
  4. customPurification
  5. customCrystallization from ethanol

Sources & evidence

ORD record
ord-361b824ab7af491dbd757d8b34510522
Source dataset
uspto-grants-1998_10
Patent number
US05821372

Reaction notes

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