Water → 4-azidomethyl-N-methyl-benzenesulfonamide

HRID 2382934Notes

Reaction equation

HRID 2382934 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-a683276f8e1740a6a6b129bb4515633e
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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