Methanol → 2-Aminothiophene-3-carboxamide

HRID 2116576Notes

Reaction equation

HRID 2116576 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].CO>O.C(N(CC)CC)C>[NH2:10][C:9]1[S:3][CH:2]=[CH:7][C:11]=1[C:12]([NH2:14])=[O:13]

Participants

6

Reactant 3

HCID 887MethanolHCID 7898CyanoacetamideHCID 983301,4-Dithiane-2,5-diol

Product 1

HCID 6994952-Aminothiophene-3-carboxamideYield 141.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
37.5 °C

Procedure

2,5-Dihydroxy-1,4-dithiane (76 g) and cyanoacetamide (84 g) were added to a mixture of methanol (180 mL), water (10 mL) and triethylamine (10 g). The resulting mixture was heated at 35-40° C. for about 30 minutes while stirring, and then heated to 50-60° C. for an additional 30 minutes with stirring. The reaction mixture was then cooled to room temperature and poured into a mixture of ice (100 g)/water (300 mL). A fine precipitate formed upon addition, which was filtered and dried overnight to give 100.6 g of the title compound as a pale gray powder ((M+H)+=143, M.P.=159.0-159.6° C.).

Workup

  1. temperatureheated to 50-60° C. for an additional 30 minutes
  2. stirringwith stirring
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. customA fine precipitate formed upon addition, which
  5. filtrationwas filtered
  6. customdried overnight

Sources & evidence

ORD record
ord-c90a63072a2b48a9aff3cb0c93d48187
Source dataset
uspto-grants-2008_10
Patent number
US07439247B2

Reaction notes

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