Sodium Bicarbonate → HCID 66789617, compound

HRID 1672265Notes

Reaction equation

HRID 1672265 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14]3[CH:15]=[CH:16][C:17]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]=3[O:12][C:11]([CH3:25])([CH3:24])[C:10]2=[O:26])=[CH:5][CH:4]=1.B(Br)(Br)Br.ClCCl.C(=O)([O-])O.[Na+]>ClCCl.C(=O)=O.CC(C)=O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14]3[CH:15]=[CH:16][C:17]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]=3[O:12][C:11]([CH3:24])([CH3:25])[C:10]2=[O:26])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 24744483HCID 24744483, compound

Product 1

HCID 66789617HCID 66789617, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18522661Acetone cardiceSolvent

Procedure

To a solution of N-[4-(4-methoxyphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H -1,4-benzoxazin-7-yl]methanesulfonamide (compound obtained in Example 14, 40 mg) in dichloromethane (5 mL) was added dropwise boron tribromide-dichloromethane solution (1.0 M, 0.32 mL) under cooling in dry ice-acetone bath. The reaction mixture was stirred at room temperature for 5.5 hours, and thereto was added an aqueous saturated sodium hydrogencarbonate solution. The mixture was extracted with chloroform and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=4/1→3/7) to give N-[4-(4-hydroxyphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide (35 mg) as a colorless powder.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=4/1→3/7)

Sources & evidence

ORD record
ord-7a09788b163d4229bd455247efd1f872
Source dataset
uspto-grants-2011_08
Patent number
US07998956B2

Reaction notes

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