Ammonium formate → HCID 86747132, compound

HRID 266476Notes

Reaction equation

HRID 266476 reaction equation
C([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([O:26][CH3:27])[C:14]([CH2:23][CH:24]=[CH2:25])=[CH:15][C:16]=2[O:20][CH2:21][CH3:22])[S:9]1(=[O:11])=[O:10])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH4+:8].[CH2:21]([O:20][C:16]1[CH:15]=[C:14]([CH2:23][CH2:24][CH3:25])[C:13]([O:26][CH3:27])=[C:12]2[C:17]=1[C:18](=[O:19])[NH:8][S:9]2(=[O:10])=[O:11])[CH3:22]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 700516382-Benzyl-4-ethoxy-6-allyl-7-methoxysaccharin

Product 1

HCID 86747132HCID 86747132, compoundYield 201.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

By the method of part D of Example 45 2-benzyl-4-ethoxy-6-allyl-7-methoxysaccharin (2.35 g) was simultaneously debenzylated and hydrogenated with ammonium formate (1.51 g) and palladium on carbon (10%, 1.25 g) in methanol (70-100 mL) affording 4-ethoxy-6-propyl-7-methoxysaccharin ammonium salt (1.94 g), phenylthiomethylation of which with chloromethyl phenyl sulfide (0.95 g) in dimethylformamide and purification of the product (a yellow oil, 2.67 g) by column chromatography on silica gel using dichloromethane-hexane (80:20) as eluant afforded 2-phenylthiomethyl-4-ethoxy-6-propyl-7-methoxysaccharin, 0.85 g, 34% yield.

Sources & evidence

ORD record
ord-9fea45d310e74706a2a28330bc556983
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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