Sulfuryl chloride → 2-Chloromethyl-4-isopropyl-6-hydroxysaccharin

HRID 129047Notes

Reaction equation

HRID 129047 reaction equation
[CH:1]([C:4]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:24])[N:7]([CH2:16]SC1C=CC=CC=1)[S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2].S(Cl)([Cl:28])(=O)=O>C(Cl)Cl>[Cl:28][CH2:16][N:7]1[C:6](=[O:24])[C:5]2[C:11](=[CH:12][C:13]([OH:15])=[CH:14][C:4]=2[CH:1]([CH3:3])[CH3:2])[S:8]1(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 103166544-Isopropyl-6-hydroxy-2-phenylthiomethylsaccharin

Product 1

HCID 102662002-Chloromethyl-4-isopropyl-6-hydroxysaccharin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-isopropyl-6-hydroxy-2-phenylthiomethylsaccharin (1.78 g) in methylene chloride was treated with sulfuryl chloride (0.43 mL, 0.73 g) to afford 1.2 g 84%) of 2-chloromethyl-4-isopropyl-6-hydroxysaccharin, m.p. 149°-150° C.

Sources & evidence

ORD record
ord-5aee0282e98242f8b42122bfe57ee5a4
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Reaction notes

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