Chloroacetamide → HCID 15009012, compound

HRID 981070Notes

Reaction equation

HRID 981070 reaction equation
[OH-].[Na+].[C:3]([S:6][CH2:7][C:8]1[NH:9][C:10](=[O:13])[S:11][CH:12]=1)(=O)N.ClC[C:16]([NH2:18])=[O:17]>O>[C:16]([CH2:3][S:6][CH2:7][C:8]1[NH:9][C:10](=[O:13])[S:11][CH:12]=1)(=[O:17])[NH2:18]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 14798Sodium HydroxideHCID 15009008HCID 15009008, compound

Product 1

HCID 15009012HCID 15009012, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.0 ml of 10N (40%) sodium hydroxide solution are added dropwise to a suspension containing 5.7 g (0.03 mol) of 4-carbamoylmercaptomethyl-2(3H)-thiazolone [compound of the formula (Ib)] in 27 ml of water and 18 ml of ethanol at 25° to 30° C. while bubbling an inert gas through the mixture. After 15 minutes, 3.0 g (0.032 mol) of chloroacetamide are added to the reaction mixture which is then stirred for 16 hours. After filtering off the insoluble material, the filtrate is acidified by adding 5 ml of glacial acetic acid. The crystalline product is filtered, washed with isopropanol and dried to obtain 4.04 g (66.0%) of the named compound, m.p.: 151°-153° C. The active ingredient content of the substance is 99.4% based on titration with alkaline metal hydroxide.

Workup

  1. custom18 ml of ethanol at 25° to 30° C. while bubbling an inert gas through the mixture
  2. filtrationAfter filtering off the insoluble material
  3. additionby adding 5 ml of glacial acetic acid
  4. filtrationThe crystalline product is filtered
  5. washwashed with isopropanol
  6. customdried

Sources & evidence

ORD record
ord-a2ac9f3b36544da7a08ee3b914e34f59
Source dataset
uspto-grants-1991_02
Patent number
US04990524

Reaction notes

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