Cyanoacetamide → 2-Aminothiophene-3-carboxamide

HRID 606498Notes

Reaction equation

HRID 606498 reaction equation
O[CH:2]1[CH2:7]SC(O)C[S:3]1.[C:9]([CH2:11][C:12]([NH2:14])=[O:13])#[N:10].C(N(CC)CC)C>C(O)C>[NH2:10][C:9]1[S:3][CH:2]=[CH:7][C:11]=1[C:12]([NH2:14])=[O:13]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8471TriethylamineHCID 983301,4-Dithiane-2,5-diol

Product 1

HCID 6994952-Aminothiophene-3-carboxamideYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2,5-dihydroxy-1,4-dithiane (11.8 g, 155 mmol), cyanoacetamide (17.0 g, 202 mmol) and triethylamine (20 ml) in ethanol (100 mL) was stirred under heating at 70° C. for 4 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure to an about half volume. Water was added to the residue, the precipitated insoluble material was collected by filtration, and the solid was washed with water to give 2-amino-3-thiophenecarboxamide as a brown powder (15.3 g, 69%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure to an about half volume
  3. additionWater was added to the residue
  4. filtrationthe precipitated insoluble material was collected by filtration
  5. washthe solid was washed with water

Sources & evidence

ORD record
ord-92d1389d9369420db15f4d1a383f6c05
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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