5-Chloro-2-methylphenyl isothiocyanate → 2-[3-(5-Chloro-2-methylphenyl)-1-phenyl-thioureido]-acetic acid ethyl ester

HRID 742264Notes

Reaction equation

HRID 742264 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:24])=[C:19]([N:21]=[C:22]=[S:23])[CH:20]=1>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:22]([NH:21][C:19]1[CH:20]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=1[CH3:24])=[S:23])[CH3:2]

Participants

4

Reactant 2

HCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 75190N-Phenylglycine ethyl ester

Product 1

HCID 543145622-[3-(5-Chloro-2-methylphenyl)-1-phenyl-thioureido]-acetic acid ethyl esterYield 94.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of N-phenyl glycine ethyl ester (8.95 g), 5-chloro-2-methylphenylisothiocyanate (9.18 g), and chloroform (200 mL) was heated at reflux for 24 hours. The solvent was evaporated. The residue was crystallized from ethyl acetate/hexane mixture. The solid was collected and dried to give 17.2 g of 2-[3-(5-chloro-2-methylphenyl)-1-phenyl -thioureido]-acetic acid ethyl ester as a white solid, m.p. 148°-150° C. Anal. Calcd. for. C18H19Cl N2O S: C, 59.58; H, 5.28; N, 7.72. Found: C, 59.79; H, 5.38; N, 7.65. Mass spectrum (EI, M.+) m/z 262/264.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was evaporated
  4. customThe residue was crystallized from ethyl acetate/hexane mixture
  5. customThe solid was collected
  6. customdried

Sources & evidence

ORD record
ord-ce9a76d4982e48618af581e1e709f5ce
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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