Ethanol → 3-Chloro-4-(pyrrolidin-1-ylsulfonyl)benzoic acid

Reaction equation

[Cl:1][C:2]1[CH:3]=C([CH:7]=[CH:8][C:9]=1[S:10]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11])C#N.[OH-:18].[Na+].ClCl.[CH2:22]([OH:24])[CH3:23]>>[Cl:1][C:2]1[CH:3]=[C:23]([CH:7]=[CH:8][C:9]=1[S:10]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11])[C:22]([OH:18])=[O:24]

Participants

Reactant 4

HCID 702Ethanol

HCID 14798Sodium Hydroxide

HCID 24526Chlorine

HCID 693125003-Chloro-4-(pyrrolidin-1-ylsulfonyl)benzonitrile

Product 1

HCID 693111543-Chloro-4-(pyrrolidin-1-ylsulfonyl)benzoic acidYield 89%

Procedure

Prepared analogously to Example 1f from 3-chloro-4-(pyrrolidin-1-ylsulfonyl)benzonitrile and sodium hydroxide solution in ethanol. Yield: 89% of theory; C11H21ClNO4S (289.74); mass spectrum: (M+H)+=290/292 (chlorine isotope).

Sources & evidence

ORD record: ord-bdb21e8938ca48128aaa1d11f8d3d6e9
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326791B2

Reaction notes

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