Phosphorus pentachloride → Benzyl [2-(chlorosulfonyl)ethyl]carbamate

HRID 1815934Notes

Reaction equation

HRID 1815934 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][S:14]([OH:17])(=O)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:19]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][S:14]([Cl:19])(=[O:17])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 154820532-{[(Benzyloxy)carbonyl]amino}ethane-1-sulfonic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(N-benzyloxycarbonylamino)ethanesulfonic acid (0.6 g; 2.31 mmol) was suspended in dry toluene (6 mL) and PCl5 was added (0.65 g; 3.11 mmol). The mixture was refluxed for 2 h, until complete dissolution of the reagents. After cooling at room temperature, the solvent was evaporated off under vacuum to give the crude 2-(N-benzyloxycarbonylamino)-ethanesulfonyl chloride pure enough for the next step.

Workup

  1. temperatureThe mixture was refluxed for 2 h, until complete dissolution of the reagents
  2. customthe solvent was evaporated off under vacuum

Sources & evidence

ORD record
ord-96dad23c22f14b7aba9bdc59f93a87dd
Source dataset
uspto-grants-2005_04
Patent number
US06881755B2

Reaction notes

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