Sulfuryl chloride → HCID 10446001, compound

HRID 1768695Notes

Reaction equation

HRID 1768695 reaction equation
C1(S[CH2:8][N:9]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH:21]([CH3:23])[CH3:22])[S:10]2(=[O:12])=[O:11])C=CC=CC=1.S(Cl)([Cl:27])(=O)=O>ClCCl>[Cl:27][CH2:8][N:9]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH:21]([CH3:23])[CH3:22])[S:10]1(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 10337759HCID 10337759, compound

Product 1

HCID 10446001HCID 10446001, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenylthiomethyl-4-isopropylsaccharin (53.5 g), sulfuryl chloride (40 mL, 67.2 g) and dichloromethane (250 mL) were mixed with stirring at room temperature. The mixture underwent a slightly exothermic reaction and was allowed to stand for 17 hours at room temperature, then stripped of volatiles. The residue crystallized with hexane in three crops (33.65 g, m.r. 101°-102° C.; 3.45 g, m.r. 100°-101° C.; 0.45 g, m.r. 99°-100° C.; total 38.55 g, 91% yield). The three crops were combined and recrystallized from isopropyl alcohol (30 mL)-cyclohexane (270 mL) affording 2-chloromethyl-4-isopropylsaccharin in two crops (33.5 g, m.r. 101°-102.5° C.; 2.65 g, m.r. 100°-101° C.).

Workup

  1. customThe mixture underwent a slightly exothermic reaction
  2. customThe residue crystallized with hexane in three crops (33.65 g, m.r. 101°-102° C.; 3.45 g, m.r. 100°-101° C.; 0.45 g, m.r. 99°-100° C.; total 38.55 g, 91% yield)
  3. customrecrystallized from isopropyl alcohol (30 mL)-cyclohexane (270 mL)

Sources & evidence

ORD record
ord-f9c5af4faa7b4b62b00536df50c56985
Source dataset
uspto-grants-1995_01
Patent number
US05378720

Reaction notes

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