Triethylamine → 1-Butyl-3-(3-chloro-6-methylphenyl)-2-thioxo-imidazolidin-4-one

HRID 399605Notes

Reaction equation

HRID 399605 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]([OH:9])=O)[CH2:2][CH2:3][CH3:4].[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:20])=[C:15]([N:17]=[C:18]=[S:19])[CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:5]1[CH2:6][C:7](=[O:9])[N:17]([C:15]2[CH:16]=[C:11]([Cl:10])[CH:12]=[CH:13][C:14]=2[CH3:20])[C:18]1=[S:19])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 413376NoName_600

Product 1

HCID 189682151-Butyl-3-(3-chloro-6-methylphenyl)-2-thioxo-imidazolidin-4-oneYield 40.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of N-butyl glycine (12.0 g), 5-chloro-2-methylphenyl-isothiocyanate (9.15 g), triethyl amine (12.0 g) and chloroform (200 mL) was heated at reflux for 5 hours. The solvent was evaporated. The residue was treated with diethyl ether (400 mL). The mixture was filtered. The solid was washed with diethyl ether then discarded. The filtrate was evaporated to dryness. Crystallization from ethanol afforded the title compound (6.0 g) as a tan solid, m.p. 102°-103° C. Anal. Calcd. for. C14H17Cl N2 O S: C, 56.65; H, 5.77; N, 9.44. Found: C, 56.41; H, 5.97; N, 9.36. Mass spectrum (EI, M.+) m/z 296/298.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was evaporated
  4. additionThe residue was treated with diethyl ether (400 mL)
  5. filtrationThe mixture was filtered
  6. washThe solid was washed with diethyl ether
  7. customThe filtrate was evaporated to dryness
  8. customCrystallization from ethanol

Sources & evidence

ORD record
ord-3de2ab28e87e4c4c8b90af5e70b6690b
Source dataset
uspto-grants-1998_10
Patent number
US05821372

Reaction notes

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