Triethylamine → 5-Chloro-2-methoxyphenyl-1-methyl-2-thioxo-imidazolidin-4-one

HRID 742227Notes

Reaction equation

HRID 742227 reaction equation
Cl.C([O:4][C:5](=O)[CH2:6][NH:7][CH3:8])C.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15]([N:17]=[C:18]=[S:19])[CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15]([N:17]2[C:5](=[O:4])[CH2:6][N:7]([CH3:8])[C:18]2=[S:19])[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 7371654-Chloro-2-isothiocyanato-1-methoxy-benzene

Product 1

HCID 190697455-Chloro-2-methoxyphenyl-1-methyl-2-thioxo-imidazolidin-4-oneYield 87.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of sarcosine ethyl ester hydrochloride (7.68 g), 5-chloro-2-methoxyphenyl-isothiocyanate (10.0 g), triethylamine (10.0 g) and chloroform (150 mL) was heated at reflux for 4.5 hours. The mixture was cooled to ambient temperature. The precipitated solid was collected, washed with chloroform and air dried to give the title compound (11.8 g) as an off-white solid, m.p. 245°-247° C. Anal. Calcd. for C11H11Cl N2O S: C, 48.80; H, 4.10; N,10.35. Found: C, 48.42; H, 3.96; N, 10.33. Mass spectrum (El, M.+) m/z 270.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. customThe precipitated solid was collected
  4. washwashed with chloroform and air
  5. customdried

Sources & evidence

ORD record
ord-439962a4409046cf9808ce03d0c5b20e
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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