Cyanoacetamide → 2-Aminothiophene-3-carboxamide

HRID 1162747Notes

Reaction equation

HRID 1162747 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>CCO>[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-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,5-dihydroxy-1,4-dithiane (5.83 g, 38.3 mmol), 2-cyanoacetamide (8.4 g, 99.1 mmol) and triethylamine (10 mL, 71.9 mmol) in EtOH (30 mL) was heated at 70° C. for 2 h then allowed to stand overnight. The reaction mixture was reduced by half in vacuo and the solution cooled with ice to produce a precipitate. The solid was filtered off, washing with heptane (200 mL) to give product as a brown solid (7.12 g, 50.1 mmol, 51

Workup

  1. temperaturethe solution cooled with ice
  2. customto produce a precipitate
  3. filtrationThe solid was filtered off
  4. washwashing with heptane (200 mL)
  5. customto give product as a brown solid (7.12 g, 50.1 mmol, 51

Sources & evidence

ORD record
ord-d2d9a785db134a96b9b733289caf62a2
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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