Sulfuryl chloride → 2-Chloromethyl-4-sec-butyl-6-methoxysaccharin

HRID 129054Notes

Reaction equation

HRID 129054 reaction equation
C1(S[CH2:8][N:9]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15]([O:25][CH3:26])=[CH:16][C:17]=3[CH:21]([CH2:23][CH3:24])[CH3:22])[S:10]2(=[O:12])=[O:11])C=CC=CC=1.S(Cl)([Cl:30])(=O)=O>C(Cl)Cl>[Cl:30][CH2:8][N:9]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([O:25][CH3:26])=[CH:16][C:17]=2[CH:21]([CH2:23][CH3:24])[CH3:22])[S:10]1(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 677843062-Phenylthiomethyl-4-sec-butyl-6-methoxysaccharin

Product 1

HCID 677844242-Chloromethyl-4-sec-butyl-6-methoxysaccharin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylthiomethyl-4-sec-butyl-6-methoxysaccharin (2.6 g) in CH2Cl2 (20 mL) was added sulfuryl chloride (0.7 mL). The mixture was stirred at ambient temperature overnight, and the solvent was removed in vacuo. The residue was treated with hexane and the mixture was sonicated for 6 hours. A precipitate formed with a collected by filtration to afford 1.33 g of 2-chloromethyl-4-sec-butyl-6-methoxysaccharin.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was treated with hexane
  3. customthe mixture was sonicated for 6 hours
  4. customA precipitate formed with
  5. filtrationa collected by filtration

Sources & evidence

ORD record
ord-ef59548279a04bc8b839414dd4760a56
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Reaction notes

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