2-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide → 2-(1-Phenyltetrazol-5-yl)thiomethyl-4-isopropyl-6-methoxysaccharin

HRID 1769027

Reaction equation

HRID 1769027 reaction equation
Cl[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9]([O:18][CH3:19])=[CH:10][C:11]=2[CH:15]([CH3:17])[CH3:16])[S:4]1(=[O:6])=[O:5].[Na].[C:21]1([N:27]2[C:31]([SH:32])=[N:30][N:29]=[N:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[C:21]1([N:27]2[C:31]([S:32][CH2:2][N:3]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][C:9]([O:18][CH3:19])=[CH:10][C:11]=4[CH:15]([CH3:17])[CH3:16])[S:4]3(=[O:6])=[O:5])=[N:30][N:29]=[N:28]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxideHCID 178527989HCID 178527989, compound

Product 1

HCID 98897272-(1-Phenyltetrazol-5-yl)thiomethyl-4-isopropyl-6-methoxysaccharinYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloromethyl-4-isopropyl-6-methoxysaccharin (0.25 g) and 1-phenyltetrazole-5-thiol sodium salt (0.173 g) in dimethylformamide (10 mL) was heated at 60°-80° C. for 8 hours, then poured into ice-water containing saturated aqueous sodium bicarbonate. The resulting mixture was extracted with ether. The ether extract was washed with water and saturated aqueous sodium chloride, passed through silica gel and stripped of ether affording 2-(1-phenyltetrazol-5-yl)thiomethyl-4-isopropyl-6-methoxysaccharin as a foam (0.3 g, 83% yield).

Workup

  1. temperaturewas heated at 60°-80° C. for 8 hours
  2. extractionThe resulting mixture was extracted with ether
  3. extractionThe ether extract
  4. washwas washed with water and saturated aqueous sodium chloride

Sources & evidence

ORD record
ord-aa4e654b348e4912a9b6fd22d1edd2ca
Source dataset
uspto-grants-1995_01
Patent number
US05380737

Linked notes

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