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

HRID 1957315Notes

Reaction equation

HRID 1957315 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 (EI, 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-c6671fdbb8d6412cb3176caceccf0702
Source dataset
uspto-grants-1998_07
Patent number
US05783707

Reaction notes

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