Benzaldehyde → HCID 15675940, compound

HRID 1460563Notes

Reaction equation

HRID 1460563 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([CH3:13])[C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:14]([NH:1][C:2]1[C:11]([F:12])=[C:10]([CH3:13])[C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 15675935HCID 15675935, compound2×

Product 1

HCID 15675940HCID 15675940, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-amino-5-fluoro-4-methyl-2-benzoxazolone (Example 7 0.43 g, 2.40 mmoles) and benzaldehyde (0.26 g, 2.40 mmoles) in ethanol (2 ml) was refluxed for 2.5 hours. After cooling, the precipitated product was collected and washed with cold ethanol. To a mixture of the precipitate (0.63 g) and ethanol (8 ml) was added portionwise sodium borohydride (300 mg) at room temperature under stirring. Stirring continued for 15 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate and evaporated to dryness. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexane (1:4 by volume) to give the title compound (0.56 g). Recrystallization from methanol gave 0.44 g (68%) of the title compound as pale orange needles: m.p. 204°-206° C.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. temperatureAfter cooling
  3. customthe precipitated product was collected
  4. washwashed with cold ethanol
  5. additionTo a mixture of the precipitate (0.63 g) and ethanol (8 ml)
  6. additionwas added portionwise sodium borohydride (300 mg) at room temperature
  7. stirringStirring
  8. additionThe reaction mixture was diluted with ethyl acetate
  9. washwashed with water
  10. extractionThe aqueous phase was extracted twice with ethyl acetate
  11. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  12. customevaporated to dryness
  13. customThe residue was purified by column chromatography on silica gel
  14. washeluting with ethyl acetate/hexane (1:4 by volume)

Sources & evidence

ORD record
ord-c1241f7c52fa42aea5cef84bdca2a7aa
Source dataset
uspto-grants-1991_12
Patent number
US05071863

Reaction notes

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