4-Aminobenzoic Acid → 4-(Methylsulfonamido)benzoic acid

HRID 1090355

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13]>>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][S:12]([CH3:11])(=[O:14])=[O:13])=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

Reactant 2

HCID 9784-Aminobenzoic Acid

HCID 31297Methanesulfonyl chloride2×

Product 1

HCID 2506534-(Methylsulfonamido)benzoic acid

Procedure

4-Aminobenzoic acid is reacted with methanesulfonyl chloride (Compound 19) to give N-(4-carboxyphenyl)methanesulfonamide. 2-Triethylsilyl-4-furaldehyde (Compound 18) is reacted with N-(4-carboxyphenyl)methanesulfonamide and lithium diisopropylamide. The resulting 4-[1-hydroxy-2-N-(4-carboxyphenyl)sulfonamido]-ethyl-2-triethylsilylfuran is esterified with dodecanoyl chloride in the presence of triethylamine. Oxidizing this ester with singlet oxygen, under conditions as in Example 1, gives the title furanone.

Sources & evidence

ORD record: ord-d4e193d1439540859dd74b7465bb646f
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05081261

Linked notes

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