Chloroacetyl chloride → HCID 20316057, compound

HRID 973109Notes

Reaction equation

HRID 973109 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][CH2:16][N:17]1[C:21](=[O:22])[CH2:20][S:19][C:18]1=[O:23].[Cl:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)(Cl)Cl>[Cl:24][CH2:25][C:26]([N:15]([CH2:16][N:17]1[C:21](=[O:22])[CH2:20][S:19][C:18]1=[O:23])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH3:7])=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 1379704HCID 1379704, compound

Product 1

HCID 20316057HCID 20316057, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 7 g of anhydrous potassium carbonate, 7.3 g of N-(2-methoxyphenylaminomethyl)-2,4-thiazolidinedione, and 5.3 g of chloroacetyl chloride in 50 ml of chloroform was cooled in an ice bath and stirred at ambient temperature for 48 hrs. The resulting precipitate was filtered, washed with water and recrystallized from nitromethane-ethanol to give 5.6 g of 2-chloro-N-(2,4-dioxothiazolidin-3-ylmethyl)-N-(2-methoxyphenyl)acetamide; mp 188°-191° C; M+ = 328.

Workup

  1. temperaturewas cooled in an ice bath
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customrecrystallized from nitromethane-ethanol

Sources & evidence

ORD record
ord-a1b8252981a04b2ab757b5ea37221408
Source dataset
uspto-grants-1977_10
Patent number
US04055410

Reaction notes

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