Phosphorus oxychloride → Ethyl (chlorosulfonyl)acetate

HRID 2396093Notes

Reaction equation

HRID 2396093 reaction equation
[S:1]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(O)(=[O:3])=[O:2].O=P(Cl)(Cl)[Cl:13]>>[Cl:13][S:1]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])=[O:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12216623Ethyl sulfoacetate

Product 1

HCID 12225100Ethyl (chlorosulfonyl)acetate

Procedure

1H NMR (CDCl3):δ1.35 (t, 3H), 4.1 (s, 2H), 4.25 (q, 2H). Amixture of ethyl sulfoacetate (16.82 g, 100 mM) and POCl3 (30.67 g, 200 mM) was heated at 125° C. for 5 hours. The mixture was cooled and filtered, and excess POCl3 was removed to give ethyl chlorosulfonylacetate. The ethyl chlorosulfonylacetate (8.18 g, 43.83 mM) was added dropwise with stirring to a solution of 2,6-diisopropylaniline (15.54 g, 87.66 mM) in 50 mL CH2Cl2 maintained at 0° C. The mixture was stirred at room temperature for an additional 18 hours. The solvent was removed and the residue was redissolved in 100 mL ethyl acetate and washed with 1N HCl and brine. The ethyl acetate was evaporatedand the pure compound was isolated by chromatography over silica gel (EtOAc/hexane, 1:4 as eluant) as a white powder identified as ethyl (2,6-diisopropylphenylsulfamoyl)acetate, 7.0 g (≈50%), mp 74°-77° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customexcess POCl3 was removed

Sources & evidence

ORD record
ord-ef6da34a09e74f8c8221b2c00982a6b0
Source dataset
uspto-grants-1996_02
Patent number
US05491170

Reaction notes

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