Chloroacetanilide → N-phenyl-2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetamide

HRID 1764452Notes

Reaction equation

HRID 1764452 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]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17]>CN(C)C=O>[C:19]1([NH:18][C:16]([CH2:15][N:4]2[C:5](=[O:6])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:1]2(=[O:2])=[O:3])=[O:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 11485ChloroacetanilideHCID 24181110Benzosulfinide sodium; Garantose sodium

Product 1

HCID 677934N-phenyl-2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetamideYield 62.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 22.6g (0.11 mole) of sodium saccharin and 16.7g (0.1 mole) of N-chloroacetylaniline in 150ml of dimethylformamide is heated on a steam bath for one hour, allowed to stir at room temperature for 16 hrs. and poured into ice-water. The resulting precipitate is collected and dissolved in dichloromethane. This solution is dried over magnesium sulfate, and the solvent is evaporated. The residue is recrystallized from methanol to give 19.9g of product, mp. 180°-182° C. EXAMPLE 2 ##STR5##

Workup

  1. customThe resulting precipitate is collected
  2. dissolutiondissolved in dichloromethane
  3. dry with materialThis solution is dried over magnesium sulfate
  4. customthe solvent is evaporated
  5. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-57a689350faf440db8502e219738db50
Source dataset
uspto-grants-1978_09
Patent number
US04116964

Reaction notes

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