Sulfuryl chloride → HCID 70047012, compound

HRID 266468Notes

Reaction equation

C1(S[CH2:8][N:9]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15]([O:26][CH3:27])=[C:16]([O:24][CH3:25])[C:17]=3[CH2:21][CH2:22][CH3:23])[S:10]2(=[O:12])=[O:11])C=CC=CC=1.S(Cl)([Cl:31])(=O)=O>>[Cl:31][CH2:8][N:9]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([O:26][CH3:27])=[C:16]([O:24][CH3:25])[C:17]=2[CH2:21][CH2:22][CH3:23])[S:10]1(=[O:12])=[O:11]

Participants

Reactant 2

HCID 24648Sulfuryl chloride

HCID 70044810HCID 70044810, compound

Product 1

HCID 70047012HCID 70047012, compoundYield 97%

Procedure

By the method of Example 22A 3,4-dimethoxy-2-propyl-N,N-dimethylbenzamide (9.2 g) was aminosulfonylated with sulfur dioxide and hydroxylamine-O-sulfonic acid (5.6 g) to give 2-aminosulfonyl-4,5-dimethoxy-6-propyl-N,N-dimethylbenzamide (7.4 g, 63% yield), which was cyclized in quantititive yield to 4-propyl-5,6-dimethoxysaccharin, phenylthiomethylation of which with chloromethyl phenyl sulfide (1.42 mL) gave 2-phenylthiomethyl-4-propyl-5,6-dimethoxy-saccharin (4.07 g), reaction of part (3.59 g) of which with sulfuryl chloride (2.12 mL) gave 2-chloromethyl-4-propyl-5,6-dimethoxysaccharin, 2.84 g, 97% yield.

Workup

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Sources & evidence

ORD record: ord-f6a0c44dc9ba41fdb8ea99ede754a689
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650422

Reaction notes

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