Benzyl Bromide → HCID 101859068, compound

HRID 58859Notes

Reaction equation

HRID 58859 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=O>C(#N)C.CCOC(C)=O>[CH2:7]([N:23]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:15]=[CH:27][S:24]1(=[O:26])=[O:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 115793042-(Methylsulfonamido)benzaldehyde

Product 1

HCID 101859068HCID 101859068, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Cesium carbonate (18.0 g, 55 mmol) and benzyl bromide (6.6 mL, 55 mmol) were added to a solution of N-(2-formylphenyl)methanesulfonamide (5.50 g, 27.6 mmol) in acetonitrile (120 mL). The reaction mixture was heated at 60° C. for 16 h and then cooled to ambient temperature. The mixture was diluted with EtOAc (200 mL) and filtered. The filtration cake was washed with EtOAc (200 mL) and the combined organics were concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:5) to afford 1-benzyl-1H-benzo[c][1,2]thiazine 2,2-dioxide (6.5 g, 87% yield) as a colorless oil.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered
  3. washThe filtration cake was washed with EtOAc (200 mL)
  4. concentrationthe combined organics were concentrated
  5. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:5)

Sources & evidence

ORD record
ord-e6c18c22b4ee4b0492e7c9404d37af24
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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