Cyanoacetamide → 2-Aminothiophene-3-carboxamide

HRID 1010821Notes

Reaction equation

HRID 1010821 reaction equation
[S:1]1CC(O)S[CH2:3][CH:2]1O.[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:1][CH:2]=[CH:3][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 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1,4-dithian-2,5-diol (4.56 g, 30 mmole) and 2-cyanoacetamide (2.52 g, 30 mmole) were combined in ethanol (50 ml). Triethylamine (6 ml) was added and heated to 70° C. for 1 hour. The volume of solvent was reduced under vacuum, and the product was isolated by filtration. Product was recrystallized from ethanol to give 2.71 g of product (yield 64%).

Workup

  1. customthe product was isolated by filtration
  2. customProduct was recrystallized from ethanol

Sources & evidence

ORD record
ord-d29932dd8477499eafd8b0fdde1194eb
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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