Triethylamine → 3-(5-Chloro-2-methoxyphenyl)-1-ethyl-2-thioxo-imidazolidin-4-one

HRID 742241Notes

Reaction equation

HRID 742241 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([N:15]=[C:16]=[S:17])[CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([N:15]2[C:5](=[O:7])[CH2:4][N:3]([CH2:1][CH3:2])[C:16]2=[S:17])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 316542N-EthylglycineHCID 7371654-Chloro-2-isothiocyanato-1-methoxy-benzene

Product 1

HCID 114375983-(5-Chloro-2-methoxyphenyl)-1-ethyl-2-thioxo-imidazolidin-4-oneYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture N-ethyl glycine (9.2 g), 5-chloro-2-methoxyphenyl-isothiocyanate (10 g), triethylamine (10.1 g), methylene chloride (150 mL) was heated at reflux for 3.5 hours. The mixture was evaporated to dryness. The residue collected, washed with hot ethanol and dried. Title compound (7.6 g) was obtained as a creamy solid, m.p. 171°-174° C. Anal. Calcd. for. C12H13Cl N2O2S: C, 50.61; H, 4.60; N, 9.84. Found: C, 50.33; H, 4.50; N, 9.69. Mass spectrum (El, M.+) m/z 284/286.

Workup

  1. temperatureat reflux for 3.5 hours
  2. customThe mixture was evaporated to dryness
  3. customThe residue collected
  4. washwashed with hot ethanol
  5. customdried

Sources & evidence

ORD record
ord-eedcbd548c4f4fe183de66f4f4ee77c9
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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