Thioacetamide → HCID 20144971, compound

HRID 648585Notes

Reaction equation

HRID 648585 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12](=O)[CH2:13]Br)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[C:16]([NH2:19])(=[S:18])[CH3:17]>COCCOC.C(O)C>[NH2:1][C:2]1[S:3][C:4]([C:12]2[N:19]=[C:16]([CH3:17])[S:18][CH:13]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 2723949ThioacetamideHCID 20145096Ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate

Product 1

HCID 20144971HCID 20144971, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate (2.35 g) and thioacetamide (1.8 g) in a mixture of 1,2-dimethoxyethane (70 ml) and ethanol (70 ml) was refluxed for 7 hours and the reaction mixture was evaporated in vacuo. To the residue was added water, and the resulting mixture was adjusted to pH 8.0 with 20% aqueous potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was washed with diethyl ether and recrystallized from ethyl acetate to give ethyl 2-amino-5-(2-methyl-4-thiazolyl)-4-thiazolecarboxylate (1.4 g). mp 197°-199° C. (dec.).

Workup

  1. temperaturewas refluxed for 7 hours
  2. customthe reaction mixture was evaporated in vacuo
  3. additionTo the residue was added water
  4. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. washThe residue was washed with diethyl ether
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9b896527296c486ea51d97e4442b9817
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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