Ethyl 2-chloroacrylate → HCID 12437476, compound

HRID 614189Notes

Reaction equation

HRID 614189 reaction equation
Cl[C:2](=[CH2:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2O[C:19](=O)[S:18][N:17]=2)=[CH:12][CH:11]=1>ClC1C=CC=CC=1Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:19][S:18][N:17]=2)=[CH:14][CH:15]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:18][N:17]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 12708Ethyl 2-chloroacrylateHCID 8194535-(4-chlorophenyl)-1,3,4-oxathiazol-2-one

Product 2

HCID 12437469HCID 12437469, compoundYield 16%HCID 12437476HCID 12437476, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 40.4 g (0.30 mol) of ethyl 2-chloroacrylate and 2.14 g (0.010 mol) of 5-(p-chlorophenyl)-1,3,4-oxathiazole-2-one in 75 g of o-dichlorobenzene was held at reflux (165°-175°) for 55 minutes, at which time gas chromatography analysis indicated about 70% reaction. The reaction mixture was allowed to cool, and the supernatant was decanted from polymeric ester. Concentration of the supernatant under vacuum, chromatography of the residue on silicic acid, and crystallizations of the various materials thus obtained gave 0.30 g (16%) of ethyl 3-(p-chlorophenyl)-4-isothiazolecarboxylate, m.p. 69°-70°, and 0.31 g (17%) of ethyl 3-(p-chlorophenyl)-5-isothiazolecarboxylate, m.p. 87°-89°.

Workup

  1. temperatureat reflux (165°-175°) for 55 minutes
  2. customabout 70% reaction
  3. temperatureto cool
  4. customthe supernatant was decanted from polymeric ester
  5. customConcentration of the supernatant under vacuum, chromatography of the residue on silicic acid, and crystallizations of the various materials
  6. customthus obtained

Sources & evidence

ORD record
ord-bfef03a92b364196a69a39a25d0d5d72
Source dataset
uspto-grants-1979_03
Patent number
US04144047

Reaction notes

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