Chloroacetyl chloride → HCID 10402623, compound

HRID 704593Notes

Reaction equation

HRID 704593 reaction equation
C(=O)(O)[O-].[K+].[CH3:6][O:7][C:8]1[CH:20]=[CH:19][C:11]([O:12][CH2:13][CH:14]2[NH:18][CH2:17][CH2:16][S:15]2)=[CH:10][CH:9]=1.[Cl:21][CH2:22][C:23](Cl)=[O:24]>O.C(OCC)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH:14]2[N:18]([C:23](=[O:24])[CH2:22][Cl:21])[CH2:17][CH2:16][S:15]2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516893Potassium BicarbonateHCID 10443660HCID 10443660, compound

Product 1

HCID 10402623HCID 10402623, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 26 g of potassium bicarbonate in 55 ml of water was added under storing stirring to a solution of 2-(4-methoxy-phenoxymethyl)thiazolidine (54,5 g) in 550 ml of ethyl acetate cooled at 0°-5° C. The mixture was added with a solution of α-chloro-acetylchloride (19,2 ml) in ethyl acetate (50 ml) for 1 hour, under strong stirring and external cooling. Stirring was continued for 2 more hours, then the phases were separated. After washing of the organic phase with water, 5% aqueous NaHCO3 and water, and drying over Na2SO4, the mixture was evaporated to dryness to give 54,5 g of 2-(4-methoxy-phenoxymethyl)-3-α-chloroacetyl-thiazolidine, m.p. 51°-53° C. (from isopropyl alcohol).

Workup

  1. temperaturecooled at 0°-5° C
  2. stirringStirring
  3. customthe phases were separated
  4. washAfter washing of the organic phase with water, 5% aqueous NaHCO3 and water
  5. dry with materialdrying over Na2SO4
  6. customthe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-89fefeac6d90453a89aed01502be90da
Source dataset
uspto-grants-1991_01
Patent number
US04988701

Reaction notes

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