Potassium Carbonate → HCID 54321425, compound
Reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[C:17]([OH:18])[C:10]=2[S:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[C:17]([O:18][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH3:22])[C:10]=2[S:9]1=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Reaction of 3.03 g (0.01 mol) of 2-benzyl-7-hydroxy-4-methoxybenzisothiazol-3-one-1-oxide (Example 26A) with 2.01 g (0.011 mol) of 2-(2-methoxyethoxy) ethyl bromide in methyl ethyl ketone in the presence of 2 g (0.015 mol) of potassium carbonate afforded 2.58 g (64%) of 2-benzyl-4-methoxy-7-[2-(2-methoxyethoxy) ethoxy]benzisothiazol-3-one-1-oxide, which, on oxidation with 1.1 g (0.0063 mol) of 3-chloroperbenzoic acid in MDC, gave 2-benzyl-4-methoxy-7-[2-(2-methoxyethoxy)-ethoxy]saccharin. Debenzylation of 0.25 g (0.0006 mol) of the product with 0.13 g (0.0021 mol) of ammonium formate in methanol in the presence of 0.25 g of 10% palladium-on-charcoal gave 0.21 g (100%) of the ammonium salt of 4-methoxy-7-[2-(2-methoxyethoxy)ethoxy]saccharin. Reaction of 1.4 g (0.004 mol) of the ammonium salt with 0.63 g (0.004 mol) of chloromethyl phenyl sulfide in DMF afforded 2-phenylthio-methyl-4 -methoxy-7-[2-(2-methoxyethoxy) ethoxy]saccharin, which, on reaction with sulfuryl chloride in MDC, afforded 0.53 g (35%) of 2-chloromethyl-4-methoxy-7-[2-(2-methoxyethoxy) ethoxy]saccharin.
Sources & evidence
- ORD record
- ord-e50a6e8c5a2843a0ba062ed2ddaa9449
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05650422
Reaction notes
Loading…