tert-Butyl chloroacetate → Tert-butyl 2-(1,1-dioxido-3-oxobenzo[D]isothiazol-2(3H)-YL)acetate

HRID 616422Notes

Reaction equation

HRID 616422 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[Na].Cl[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C)C=O>[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[N:4]1[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 66052tert-Butyl chloroacetateHCID 24181110Benzosulfinide sodium; Garantose sodium

Product 1

HCID 975263Tert-butyl 2-(1,1-dioxido-3-oxobenzo[D]isothiazol-2(3H)-YL)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 22.6g (0.11 mole) of sodium saccharin and 15g (0.1 mole) of tert-butyl α-chloroacetate in 150 ml of dimethylformamide is heated on a steam bath for 1 hour, allowed to stir at room temperature for 16 hours and poured into ice-water. The solution is dried over magnesium sulfate and the solvent is evaporated to give 24.9g of tert-butyl N-saccharinylacetate, m.p. 130°-132.5° C. This is refluxed with 300 ml of benzene and 1.4g (0.01 mole) of p-toluenesulfonic acid monohydrate to cause quantitative precipitation of 2-carboxymethylsaccharin, m.p. 212°-215° C. The completion of the reaction is established by passing a slow stream of nitrogen through the reaction mixture and into solution of bromine in carbon tetrachloride. Failure to decolorize the bromine indicates that no more isobutylene is being evolved.

Workup

  1. dry with materialThe solution is dried over magnesium sulfate
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-f5a5beeca75f4a2abce8043933a6503c
Source dataset
uspto-grants-1978_02
Patent number
US04074048

Reaction notes

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