Ethyl (chloroformyl)acetate → HCID 21488109, compound

HRID 1414587Notes

Reaction equation

HRID 1414587 reaction equation
[C:1]([O:9][CH2:10][C:11]([NH2:13])=[S:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14]([CH:16](Cl)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=O>ClC(Cl)C>[C:1]([O:9][CH2:10][C:11]1[S:12][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][N:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 110743142-Benzoyloxyethanethioamide

Product 1

HCID 21488109HCID 21488109, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 9.14 g of 2-benzoyloxythioacetamide, 9 g of ethyl α-formyl-chloroacetate and 100 ml of dichloroethane was refluxed for 4 hours and after the addition of 4.5 g of ethyl β-formyl-chloroacetate, reflux was maintained for 2 hours. The mixture was cooled and was washed first with aqueous sodium carbonate and then water. The mixture was dried and the solvent was evaporated to obtain 14 g of raw product which was chromatographed over silica gel. Elution with a benzene-ethyl acetate mixture yielded 12.5 g of ethyl 2-benzoyloxymethyl-thiazole-5-carboxylate in the form of an oil.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperaturereflux
  3. temperaturewas maintained for 2 hours
  4. temperatureThe mixture was cooled
  5. washwas washed first with aqueous sodium carbonate
  6. customThe mixture was dried
  7. customthe solvent was evaporated
  8. customto obtain 14 g of raw product which
  9. customwas chromatographed over silica gel
  10. washElution with a benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-29b99e144e8c46918076aeff4e7f5647
Source dataset
uspto-grants-1977_01
Patent number
US04001447

Reaction notes

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