Formaldehyde → 2-(Hydroxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 864726Notes

Reaction equation

HRID 864726 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].[CH2:13]=[O:14]>C(O)C>[OH:14][CH2:13][N:4]1[C:5](=[O:6])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:1]1(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 5143Saccharin

Product 1

HCID 725602-(Hydroxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following a procedure similar to that described in Preparation 2, reaction of 18.3 g (0.1 mol) of saccharin with 70 ml of 37% formalin in ethanol afforded 3.58 g (70%) of 2-hydroxymethylsaccharin. The latter (25 g, 0.117 mol) was reacted with 63.3 g (0.234 mol) of phosphorus tribromide in diethyl ether to give 29.8 g (92%) of 2-bromomethylsaccharin, mp 155°-157° C.

Sources & evidence

ORD record
ord-d42823efdc964c399520027c62d96c12
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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