4-Methoxybenzenesulfonamide → HCID 22151552, compound

HRID 703149Notes

Reaction equation

HRID 703149 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][S:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Br[CH2:26][CH2:27]CCCSC(C)(C)C(OCC)=O.COC1C=CC(S(N)(=O)=O)=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][S:18][C:19]([CH3:24])([CH3:23])[C:20]([O:22][CH2:26][CH3:27])=[O:21])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 707894-MethoxybenzenesulfonamideHCID 22151555HCID 22151555, compoundHCID 22151565HCID 22151565, compound

Product 1

HCID 22151552HCID 22151552, compoundYield 69%

Procedure

In an analogous way, there are obtained: 2. 8-(4-Methoxybenzenesulphonamido)-2,2-dimethyl-3-thiaoctanoic acid by reaction of ethyl 8-bromo-2,2-dimethyl-3-thiaoctanoate with 4-methoxybenzenesulphonamide to give (a) ethyl 8-(4-methoxybenzenesulphonamido)-2,2-dimethyl-3-thiaoctanoate; after chromatography on silica gel/cyclohexane+diethyl ether (2:1 v/v), the yield is 69% of theory; colourless oil; nD20 =1.5280 and subsequent saponification of this ester to give (b) the desired acid; yield 90% of theory; m.p. 57°-59° C. 3. 8-(3-Trifluoromethylbenzenesulphonamido)-2,2-dimethyl-3-thiaoctanoic acid by reaction of ethyl 8-bromo-2,2-dimethyl-3-thiaoctanoate with 3-trifluoromethylbenzenesulphonamide to give

Workup

  1. customIn an analogous way, there are obtained

Sources & evidence

ORD record
ord-5479a3957af04f848dd8e8678f3283ee
Source dataset
uspto-grants-1991_01
Patent number
US04981873

Reaction notes

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