Ammonium Hydroxide → 2-(Phenylmethoxy)ethanesulfonamide

HRID 2078639Notes

Reaction equation

HRID 2078639 reaction equation
[OH-].[NH4+:2].[CH2:3]([O:10][CH2:11][CH2:12][S:13](Cl)(=[O:15])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>ClCCl>[CH2:3]([O:10][CH2:11][CH2:12][S:13]([NH2:2])(=[O:15])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 641796232-Benzyloxy-ethanesulfonyl chloride

Product 1

HCID 642009082-(Phenylmethoxy)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 28% ammonium hydroxide (10 ml) was added dropwise 2-(benzyloxy)ethanesulfonyl chloride (4.1 g) in dichloromethane (10 ml) over 10 minutes under ice-cooling. The mixture was stirred at ambient temperature overnight. The organic layer was separated and the aqueous layer was extracted with dichloromethane/methanol (5/1). The combined organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=50/50) to give 2-(benzyloxy)ethanesulfonamide (1.6 g).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane/methanol (5/1)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-b88c54b646644b2da5bf35f1e027b8dc
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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