Chlorosulfamic acid → 1-[2-[(Aminosulfonyl)oxy]ethyl]-2-pyrrolidinone

HRID 1613770Notes

Reaction equation

HRID 1613770 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[S:10](Cl)(=[O:13])(=[O:12])[NH2:11]>C(Cl)Cl>[NH2:11][S:10]([O:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinone

Product 1

HCID 191086941-[2-[(Aminosulfonyl)oxy]ethyl]-2-pyrrolidinoneYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.5 g (0.05 mole) of 1-(2-hydroxyethyl)-2-pyrrolidone (Fluka) in 100 ml of methylene chloride was treated with 5.8 g (0.05 mole) of sulfamoyl chloride. The solution was stirred for 2 hr, then concentrated under vacuum. The residue was crystallized twice from 2-propanol to give 6.9 g (66%) of the title compound as white crystals, mp 110°-112° C. The compound was noted to be slightly hygroscopic.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was crystallized twice from 2-propanol

Sources & evidence

ORD record
ord-4876ba823abd4075874eba3e49a39582
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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