Formamide → HCID 21838301, compound

HRID 1740289Notes

Reaction equation

HRID 1740289 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH2:14][O:15][CH2:16][C:17]=3[C:18](OC)=[O:19])[CH:8]=2)=[N:3]1.C[O-].[Na+].C([NH2:28])=O>>[C:18]([C:17]1[CH2:16][O:15][CH2:14][C:13]=1[C:9]1[CH:8]=[C:7]([C:4]2[O:5][CH2:6][C:2]([CH3:22])([CH3:1])[N:3]=2)[CH:12]=[CH:11][CH:10]=1)(=[O:19])[NH2:28]

Participants

4

Reactant 3

HCID 713FormamideHCID 10942334Sodium MethoxideHCID 21838085HCID 21838085, compound

Product 1

HCID 21838301HCID 21838301, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 4,4-dimethyl-2-[3-(4-methoxycarbonyl-2,5-dihydrofuran-3-yl)phenyl]-4,5-dihydrooxazole (1.92 g) and sodium methoxide (0.96 g) in formamide (70 ml) was heated at 100° C. for three hours. The reaction mixture was cooled to room temperature and was poured onto ice-water. The product was extracted with ethyl acetate and the organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and acetone (5:1). The fractions containing the desired product were collected and evaporated in vacuo to give 2-[3-(4-carbamoyl-2,5-dihydrofuran-3-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionwas poured onto ice-water
  3. extractionThe product was extracted with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and acetone (5:1)
  8. additionThe fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-ac5914d6dde7414ab829b41333fa1550
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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