Ammonium Hydroxide → Phenylmethyl N-[2-(aminosulfonyl)ethyl]carbamate

HRID 2180108Notes

Reaction equation

HRID 2180108 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][S:14](Cl)(=[O:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:18].[OH-]>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][S:14]([NH2:18])(=[O:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 13255033Benzyl [2-(chlorosulfonyl)ethyl]carbamate

Product 1

HCID 11615848Phenylmethyl N-[2-(aminosulfonyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Crude 2-(N-benzyloxycarbonylamino)ethanesulfonyl chloride was dissolved in acetonitrile (10 mL). The resulting solution was cooled on an ice/water bath and a solution 1:1 of 28% NH4OH (5 mL) and acetonitrile (5 mL) was dropped therein. After stirring for 30′, the solvents were evaporated off under vacuum and the crude residue was recrystallised with methanol to give 2-(N-benzyloxycarbonylamino)ethanesulfonamide as white powder (0.51 g; 1.96 mmol).

Workup

  1. temperatureThe resulting solution was cooled on an ice/water bath
  2. customwere evaporated off under vacuum
  3. customthe crude residue was recrystallised with methanol

Sources & evidence

ORD record
ord-cc1fc6b93e3442f89386c939b88e5139
Source dataset
uspto-grants-2005_05
Patent number
US06887903B1

Reaction notes

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