Triethylamine → 2-[3-(5-Chloro-2-methoxyphenyl)-thioureido]acetamide

HRID 1449599Notes

Reaction equation

HRID 1449599 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].C(N(CC)CC)C.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:24][CH3:25])=[C:19]([N:21]=[C:22]=[S:23])[CH:20]=1>C(Cl)(Cl)Cl>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:24][CH3:25])=[C:19]([NH:21][C:22](=[S:23])[NH:2][CH2:3][C:4]([NH2:6])=[O:5])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7371654-Chloro-2-isothiocyanato-1-methoxy-benzeneHCID 2723639Glycinamide hydrochloride

Product 1

HCID 537435902-[3-(5-Chloro-2-methoxyphenyl)-thioureido]acetamideYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of glycinamide hydrochloride (5.5 g), triethyl amine (5.05 g), 5-chloro-2-methoxyphenyl-isothiocyanate (9.95 g), and chloroform (500 mL) were heated at reflux for 3 hours. The mixture was then cooled to ambient temperature and washed with water (300 mL). The organic phase was separated. Precipitate formed upon standing. The solid was collected by filtration, washed with water, then with diethyl ether and air dried to give 2-[3-(5-chloro-2-methoxyphenyl)-thioureido]acetamide (12.8 g), m.p. 166°-169° C. (dec.). This compound was used without further purification for the preparation of the title compound.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 3 hours
  3. washwashed with water (300 mL)
  4. customThe organic phase was separated
  5. customPrecipitate formed
  6. filtrationThe solid was collected by filtration
  7. washwashed with water
  8. dry with materialwith diethyl ether and air dried

Sources & evidence

ORD record
ord-14a3996b22604e6490053441ab350307
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

Loading…