Urea → Methyl 5-(2-amino-1,3-oxazol-5-yl)thiophene-3-carboxylate

HRID 2068645Notes

Reaction equation

HRID 2068645 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:13])[CH2:11]Br)[S:7][CH:6]=1)=[O:4].[NH2:14][C:15]([NH2:17])=O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[O:13][C:15]([NH2:17])=[N:14][CH:11]=2)[S:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 1176UreaHCID 539045465-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 58110273Methyl 5-(2-amino-1,3-oxazol-5-yl)thiophene-3-carboxylateYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

5-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester (0.261 g, 0.99 mmol) was dissolved in DMF (4 mL) and urea (0.131 g, 2.18 mmol) was added. The vessel was purged with nitrogen then sealed and heated by microwave irradiation at 140° C. for 10 minutes. The resultant mixture was diluted with water and extracted with ethyl acetate (×3). The organic phase was washed with lithium chloride (15% aqueous solution) then dried over sodium sulfate, filtered and evaporated to give crude 5-(2-amino-oxazol-5-yl)-thiophene-3-carboxylic acid methyl ester as an orange-brown solid (0.224 g).

Workup

  1. customThe vessel was purged with nitrogen
  2. customthen sealed
  3. additionThe resultant mixture was diluted with water
  4. extractionextracted with ethyl acetate (×3)
  5. washThe organic phase was washed with lithium chloride (15% aqueous solution)
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-2d31f7501b4b473384e03f1a0e65ddf3
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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