Sulfur Dioxide → HCID 54240182, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:16][CH2:17][CH3:18])=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:6]([N:8]([CH3:10])[CH3:9])=[O:7].[S:19](=[O:21])=[O:20].[NH2:22]OS(O)(=O)=O>>[NH2:22][S:19]([C:11]1[CH:12]=[C:13]([O:14][CH3:15])[C:3]([O:2][CH3:1])=[C:4]([CH2:16][CH2:17][CH3:18])[C:5]=1[C:6]([N:8]([CH3:10])[CH3:9])=[O:7])(=[O:21])=[O:20]Participants
4
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.
Sources & evidence
- ORD record
- ord-f965e89272204dfdb7e8521d1a07432a
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05650422
Reaction notes
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