Ethyl acetate hexane → HCID 67596817, compound

HRID 266481Notes

Reaction equation

HRID 266481 reaction equation
Cl[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[C:8]([O:20][CH3:21])[C:9]([CH3:19])=[C:10]([O:17][CH3:18])[C:11]=2[CH2:15][CH3:16])[S:4]1(=[O:6])=[O:5].[Na].[C:23]1([N:29]2[C:33]([SH:34])=[N:32][N:31]=[N:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCCCCC.C(OCC)(=O)C>CN(C)C=O>[C:23]1([N:29]2[C:33]([S:34][CH2:2][N:3]3[C:13](=[O:14])[C:12]4[C:7](=[C:8]([O:20][CH3:21])[C:9]([CH3:19])=[C:10]([O:17][CH3:18])[C:11]=4[CH2:15][CH3:16])[S:4]3(=[O:6])=[O:5])=[N:32][N:31]=[N:30]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 700523432-Chloromethyl-4-ethyl-5,7-dimethoxy-6-methylsaccharinHCID 178527989HCID 178527989, compound

Product 1

HCID 67596817HCID 67596817, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the method of Example 44 condensation of 2-chloromethyl-4-ethyl-5,7-dimethoxy-6-methylsaccharin (0.17 g) and 1-phenyltetrazol-5-thiol sodium salt (0.084 g) in dimethylformamide (4 mL) and purification of the product by flash column chromatography on silica gel using hexane-ethyl acetate (75:25) as eluant afforded 2-(1-phenyltetrazol-5-yl)thiomethyl-4-ethyl-5,7-dimethoxy-6-methylsaccharin, 0.15 g, 76% yield, mp 44°-46° C.

Sources & evidence

ORD record
ord-5d7e07e8273343f19c6ecff4004e9a95
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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