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p-Toluenesulfonic acid → 6-chloro-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-N-phenylpyridine-3-sulfonamide

HRID 45263
Notes
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Reaction equation

HRID 45263 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH2:18][CH:19]([OH:22])[CH2:20][OH:21])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO[C:25](OC)([CH3:27])[CH3:26].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH2:18][CH:19]2[CH2:20][O:21][C:25]([CH3:27])([CH3:26])[O:22]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 866597566-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide

Product 1

HCID 866597576-chloro-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-N-phenylpyridine-3-sulfonamideYield 73%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.67 g (1.96 mmol) of 6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide, 0.53 mL (4.3 mmol) of 2,2-dimethoxypropane and 37 mg of pTsOH in 4 mL of DMF is stirred for 3 hours at room temperature. The medium is taken up in 100 mL of EtOAc, washed with 50 mL of saturated NaHCO3 solution and 50 mL of water and then dried over Na2SO4, filtered and concentrated under reduced pressure. 0.54 g 6-chloro-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-N-phenylpyridine-3-sulfonamide is obtained in the form of a brown solid, which is used without further purification in the following step.

Workup

  1. washwashed with 50 mL of saturated NaHCO3 solution and 50 mL of water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-948e494dd4404503a7705e9713854a8a
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541455B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes