Sulfur Dioxide → HCID 54240182, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:18][CH2:19][CH3:20])=[C:5]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:6]([N:8]([CH2:11]C)[CH2:9]C)=[O:7].[S:21](=[O:23])=[O:22].[NH2:24]OS(O)(=O)=O>>[NH2:24][S:21]([C:13]1[CH:14]=[C:15]([O:16][CH3:17])[C:3]([O:2][CH3:1])=[C:4]([CH2:18][CH2:19][CH3:20])[C:5]=1[C:6]([N:8]([CH3:11])[CH3:9])=[O:7])(=[O:23])=[O:22]Participants
4
Procedure
By a procedure analogous to that described for Preparation 6A, 9.2 g (32.9 mmol) of 3,4-dimethoxy-2-propyl-N,N-diethylbenzamide was reacted with sulfur dioxide and 5.6 g (49.4 mmol) of hydroxylamine-O-sulfonic acid to provide 7.4 g (63%) of 2-aminosulfonyl-4,5-dimethoxy-6-propyl-N,N-dimethylbenzamide which was cyclized in quantitative yield in acetic acid and phenylthiomethylated with 1.42 mL (15 mmol) of chloromethyl phenyl sulfide to provide 4.07 g of 5,6-dimethoxy-2-phenylthiomethyl-4-propylsaccharin. Reaction of 3.59 g (8.8 mmol) of the phenylthioether with 2.12 mL (26.4 mmol) sulfuryl chloride provided 2.84 g (97%) of 2-chloromethyl-5,6-dimethoxy-4-propylsaccharin.
Sources & evidence
- ORD record
- ord-aaed7b4e8c4b48b5b8f6cea08bce494c
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05563163
Reaction notes
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