Triethylamine → 3-(5-Chloro-2-methylphenyl)-1-phenyl-2-thioxo-imidazolidin-4-one

HRID 742265Notes

Reaction equation

HRID 742265 reaction equation
C(O[C:4](=[O:24])[CH2:5][N:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[CH3:17])=[S:8])C.C(N(CC)CC)C>C(O)C>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([CH3:17])=[C:10]([N:9]2[C:4](=[O:24])[CH2:5][N:6]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:7]2=[S:8])[CH:15]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 543145622-[3-(5-Chloro-2-methylphenyl)-1-phenyl-thioureido]-acetic acid ethyl ester

Product 1

HCID 189682083-(5-Chloro-2-methylphenyl)-1-phenyl-2-thioxo-imidazolidin-4-oneYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(5-chloro-2-methylphenyl)-1-phenyl-thioureido]-acetic acid ethyl ester (9.5 g), triethyl amine (1 mL), and ethanol (150 mL) was heated at reflux for 2 hours. The mixture was concentrated to one-half volume and cooled to ambient temperature. The solid was collected and air dried to give the title compound (6.1 g) as an off-white solid, m.p. 168°-170° C. Anal. Calcd. for. C16H13Cl N2O S: C, 60.66; H, 4.14; N, 8.84. Found: C, 60.81; H, 4.16; N, 8.81. Mass spectrum (EI, M.+) m/z 316/318.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe mixture was concentrated to one-half volume
  4. customThe solid was collected
  5. customair dried

Sources & evidence

ORD record
ord-464aad4c4ae34aaa907803f081404290
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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