Triethylamine → HCID 54277983, compound

HRID 1417735Notes

Reaction equation

HRID 1417735 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[Cl:7][C:8]1[C:9]([CH3:17])=[C:10]([N:14]=[C:15]=[S:16])[CH:11]=[CH:12][CH:13]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:7][C:8]1[C:9]([CH3:17])=[C:10]([NH:14][C:15](=[S:16])[NH:2][CH2:3][C:4]([NH2:6])=[O:5])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1405041-Chloro-3-isothiocyanato-2-methylbenzeneHCID 2723639Glycinamide hydrochloride

Product 1

HCID 54277983HCID 54277983, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of glycinamide hydrochloride (6.1 g), 3-chloro-2-methylphenyl-isothiocyanate (10.1 g), triethyl amine (5.6 g), and chloroform (200 mL) was heated at reflux for 3 hours then cooled to ambient temperature. The precipitate was collected by filtration, washed with chloroform and air dried to give 2-[3-(3-chloro-2-methylphenyl)-thioureido]-acetamide (12.5 g), m.p. 162°-164° C. (dec.). This compound was used without further purification for the preparation of the title compound of step 2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with chloroform and air
  5. customdried

Sources & evidence

ORD record
ord-303ee42f7f494c5882e4b644f4d1e0fb
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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