Sulfuryl chloride → 2-Chloromethyl-4-phenylsaccharin

HRID 266442Notes

Reaction equation

HRID 266442 reaction equation
C1(SC[Cl:9])C=CC=CC=1.C1(S[CH2:17][N:18]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[S:19]2(=[O:21])=[O:20])C=CC=CC=1.S(Cl)(Cl)(=O)=O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:9][CH2:17][N:18]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[S:19]1(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 24648Sulfuryl chlorideHCID 81623Chloromethyl phenyl sulphideHCID 700446552-Phenylthiomethyl-4-phenylsaccharin

Product 1

HCID 700448392-Chloromethyl-4-phenylsaccharinYield 95%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

Following a procedure similar to that described in Example 21, the latter (0.33 g, 0.0012 mol) was reacted with 0.3 g (0.0019 mol) of chloromethyl phenyl sulfide in 15 ml of toluene in the presence of 0.08 g (0.0025 mol) of tetrabutyl-ammonium bromide and the product, 2-phenylthiomethyl-4-phenylsaccharin (0.48 g, 100%), treated with sulfuryl chloride in MDC to give 0.36 g (95%) of 2-chloromethyl-4-phenyl-saccharin.

Sources & evidence

ORD record
ord-2d8ea84c834546b488303c693d5dd84e
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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