Saccharin → 3-Dimethylamino-psi-saccharin

HRID 2419012Notes

Reaction equation

HRID 2419012 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=O)[NH:4]1)(=[O:3])=[O:2].[CH3:13][N:14]1CCNC[CH2:15]1>CN(C)P(N(C)C)(N(C)C)=O>[CH3:13][N:14]([CH3:15])[C:5]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[S:1](=[O:3])(=[O:2])[N:4]=1

Participants

4

Reactant 2

HCID 5143SaccharinHCID 531671-Methylpiperazine

Product 1

HCID 647933-Dimethylamino-psi-saccharin

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

10.0 g (54.6 mM) Saccharin and 10.9 g (109.2 mM) N-methylpiperazine are refluxed in 50 ml of hexamethylphosphoramide for 6.5 hours, and the reaction mixture is allowed to stand overnight at room temperature. The resulting precipitate is filtered off, washed with 100 ml toluene, to yield N,N-dimethyl-1,2-benzisothiazole-3-amine 1,1-dioxide. After standing for a day the combined filtrate and toluene washings yield the crystalline product which is filtered off, washed with toluene, and recrystallized from toluene. The resulting free base (3-(4-methyl-1-piperazinyl)-1,2-benzoisothiazole, 1,1-dioxide) is taken up in hot ethyl acetate and shaken with 10% aqueous HCl. The precipitated salt is filtered from the two phases, washed with ethyl acetate, and dried at 80°/vacuum to give 3.9 g of the title compound, m.p. 323°-324°.

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with 100 ml toluene

Sources & evidence

ORD record
ord-c472931b2fdd49cd9a9176561fd626a7
Source dataset
uspto-grants-1978_08
Patent number
US04104388

Reaction notes

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