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

HRID 1957314Notes

Reaction equation

HRID 1957314 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), triethyl amine (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 N2O2S: C, 48.80; H, 4.10; N, 10.35. Found: C, 48.42; H, 3.96; N, 10.33. Mass spectrum (EI, 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-a7ba08a24e9d40d796e6b016d201711c
Source dataset
uspto-grants-1998_07
Patent number
US05783707

Reaction notes

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