Ethyl cyanoacetate → Ethyl 2-aminothiophene-3-carboxylate

HRID 1264165Notes

Reaction equation

HRID 1264165 reaction equation
N1CCCCC1.O[CH:8]1[CH2:13]SC(O)C[S:9]1.[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:16]>>[NH2:16][C:15]1[S:9][CH:8]=[CH:13][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 983301,4-Dithiane-2,5-diol

Product 1

HCID 1988156Ethyl 2-aminothiophene-3-carboxylate

Procedure

Piperidine (20.7 ml) was added dropwise with stirring to a mixture of 2,5-dihydroxy-1,4-dithiane (17.5 g) and ethyl cyanoacetate (23.7 g). The mixture was stirred at room temperature for 4 hours and then allowed to stand overnight. It was filtered and the filtrate evaporated to dryness. The residue was dissolved in ether, filered and evaporated to dryness. The residue was triturated with light petroleum (b.p. 60-80° C.) containing a small amount of ethyl acetate. The gummy solid obtained was purified by silica gel column chromatography and the semi-solid product was triturated with water, filtered and washed with light petroleum (b.p. 60-80° C.) and dried to give the title product.

Workup

  1. waitto stand overnight
  2. filtrationIt was filtered
  3. customthe filtrate evaporated to dryness
  4. dissolutionThe residue was dissolved in ether
  5. customevaporated to dryness
  6. customThe residue was triturated with light petroleum (b.p. 60-80° C.)
  7. additioncontaining a small amount of ethyl acetate
  8. customThe gummy solid obtained
  9. customwas purified by silica gel column chromatography
  10. customthe semi-solid product was triturated with water
  11. filtrationfiltered
  12. washwashed with light petroleum (b.p. 60-80° C.)
  13. customdried

Sources & evidence

ORD record
ord-0d1bb0476e9b4e4eaf4e37ee73be3cbb
Source dataset
uspto-grants-2003_04
Patent number
US06541630B1

Reaction notes

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