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

HRID 1815935Notes

Reaction equation

HRID 1815935 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-9151eec6f73942f585ec44fe0fb4f750
Source dataset
uspto-grants-2005_04
Patent number
US06881755B2

Reaction notes

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