Acetic Acid → 7-(4-Chlorophenyl)-8-isopropyl-2-methyl-chromeno[7,8-d]oxazol-6-one

HRID 14509Notes

Reaction equation

HRID 14509 reaction equation
[C:1](O)(=[O:3])[CH3:2].[N:5]([C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:28])[C:13]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[C:14]([CH:18]([CH3:20])[CH3:19])[O:15]2)=[CH:10][CH:9]=1)=[N+]=[N-]>O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:13]2[C:12](=[O:28])[C:11]3[CH:10]=[CH:9][C:8]4[N:5]=[C:1]([CH3:2])[O:3][C:17]=4[C:16]=3[O:15][C:14]=2[CH:18]([CH3:20])[CH3:19])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86625618HCID 86625618, compound

Product 1

HCID 687030987-(4-Chlorophenyl)-8-isopropyl-2-methyl-chromeno[7,8-d]oxazol-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Acetic acid (20 ml) is added to polyphosphoric acid (˜25 g) heated to 80° C. The viscous solution is stirred vigorously for 5 min. 7-azido-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one (1.0 g, 2.95 mmol) is added portionwise over a period of 10 min. The reaction mixture is heated at 120° C. for 3 h, cooled to room temperature and poured into water (200 ml), and the product is extracted with CH2Cl2. The organic phase is washed with water and brine, dried (MgSO4) and filtered. Methanol (30 ml) is added, followed by partial evaporation in vacuo to give a precipitate, which is isolated by filtration.

Workup

  1. temperatureThe reaction mixture is heated at 120° C. for 3 h
  2. temperaturecooled to room temperature
  3. extractionthe product is extracted with CH2Cl2
  4. washThe organic phase is washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. additionMethanol (30 ml) is added
  8. customfollowed by partial evaporation in vacuo
  9. customto give a precipitate
  10. customwhich is isolated by filtration

Sources & evidence

ORD record
ord-8cb61e14a7b34ae9b321caf5a86fffd5
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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