Acetone → HCID 10712934, compound

HRID 326594Notes

Reaction equation

HRID 326594 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[C:13]([Br:15])[C:12]([Cl:16])=[CH:11][C:10]=1[OH:17])=O.[Cl-].[NH4+:19].S([O-])([O-])(=O)=O.[Ca+2].N.C(=O)(O)[O-].[Na+].[CH3:32][C:33]([CH3:35])=O>>[Br:15][C:13]1[C:12]([Cl:16])=[CH:11][C:10]2[O:17][C:33]([CH3:35])([CH3:32])[N:19]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:9]=2[CH:14]=1

Participants

7

Reactant 6

HCID 180Acetone2×HCID 222AmmoniaHCID 24497Calcium SulfateHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 10591244HCID 10591244, compound

Product 1

HCID 10712934HCID 10712934, compound

Conditions

Temperature
80 °C

Procedure

Into a sealed tube were placed 5-bromo-4-chloro-2-hydroxylphenyl 2-pyridyl ketone (30 g), ammonium chloride (30 g), anhydrous calcium sulfate (60 g) and acetone (500 ml) and the mixture was thoroughly mixed. Then, a solution (300 ml) of saturated ammonia in acetone was added with ice-cooling to the resultant mixture. The mixture was stirred at 80° C. for 7 hours. After air-cooling, sodium bicarbonate (60 g) was added and the mixture was stirred for 1 hour. The insoluble substance was filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane/ethyl acetate. The crude crystals thus obtained were washed with cold hexane to obtain 6-bromo-7-chloro-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (15.2 g) (Compound 88).

Workup

  1. customInto a sealed tube were placed
  2. temperatureAfter air-cooling
  3. stirringthe mixture was stirred for 1 hour
  4. filtrationThe insoluble substance was filtered off
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. washeluted with hexane/ethyl acetate
  8. customThe crude crystals thus obtained
  9. washwere washed with cold hexane

Sources & evidence

ORD record
ord-07a20620b4bd470cbef5f508bd45b14c
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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