Thioacetamide → HCID 21405589, compound

HRID 972832Notes

Reaction equation

HRID 972832 reaction equation
Br[CH:2]([CH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=O.[C:17]([NH2:20])(=[S:19])[CH3:18]>ClC(Cl)C>[CH3:18][C:17]1[S:19][C:2]([CH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:3][N:20]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 21405582HCID 21405582, compound

Product 1

HCID 21405589HCID 21405589, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

A mixture of 108 g of α-bromo-γ,γ-dicarbethoxy-butyraldehyde 300 ml of anhydrous dichloroethane and 27 g of thioacetamide was refluxed for 6 hours during which 200 ml of dichloroethane were slowly distilled and the same quantity of dichloroethane was added again to the mixture. The mixture was cooled to room temperature and 500 ml of ice water were added thereto. Concentrated ammonium hydroxide solution was added to the mixture to adjust the pH to 10-12 and the mixture was decanted. The aqueous phase was extracted with methylene chloride and the organic extracts were dried over magnesium sulfate, filtered and evaporated to dryness to obtain 110 g of diethyl 2-(2-methyl-5-thiazolyl-methyl)-propanedioate. A sample of the product was rectified to obtain the product with a boiling point of 102°C at 0.02 mm Hg.

Workup

  1. distillationwere slowly distilled
  2. additionthe same quantity of dichloroethane was added again to the mixture
  3. addition500 ml of ice water were added
  4. additionConcentrated ammonium hydroxide solution was added to the mixture
  5. customthe mixture was decanted
  6. extractionThe aqueous phase was extracted with methylene chloride
  7. dry with materialthe organic extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-c3cc08e7b2474876ac90c2df36b68725
Source dataset
uspto-grants-1977_10
Patent number
US04053618

Reaction notes

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