Water → 4-azidomethyl-N-methyl-benzenesulfonamide

HRID 1677680Notes

Reaction equation

HRID 1677680 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N-:14]=[N+:15]=[N-:16].[Na+].O>CN(C=O)C.C(OCC)(=O)C>[N:14]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[N+:15]=[N-:16]

Participants

6

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 100156454-(Bromomethyl)-N-methylbenzenesulfonamide

Product 1

HCID 596679814-azidomethyl-N-methyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred room temperature solution of 4-bromomethyl-N-methyl-benzenesulfonamide (2.70 g, 10.0 mmol) in DMF (15 mL) was added sodium azide (0.90 g, 13 mmol). The mixture was stirred at 40° C. for 16 hours. The solution was poured into water (60 mL) and diluted with ethyl acetate (100 mL). The organic layer was separated and washed with brine (30 mL), dried over sodium sulfate and concentrated in vacuo to afford 4-azidomethyl-N-methyl-benzenesulfonamide

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5e2bbb74503495e969bf074d9f0e5e9
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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