Dimethylformamide → 4-(Pyridin-4-yloxy)benzene-1-sulfonyl chloride hydrochloride

HRID 353328Notes

Reaction equation

HRID 353328 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=O)=[O:15])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.CN(C=O)C.S(Cl)([Cl:25])=O>C(#N)C>[ClH:25].[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([Cl:25])(=[O:17])=[O:15])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27604974-(4-Pyridinyloxy)benzenesulfonic acid

Product 1

HCID 27352574-(Pyridin-4-yloxy)benzene-1-sulfonyl chloride hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part C: A slurry of the sulfonic acid part B (420 g, 1.5 mol) in acetonitrile (2500 mL) and DMF (40 mL) was warmed to 75° C. under a nitrogen atmosphere and treated with thionyl chloride (243 mL, 3.3 mol) added dropwise over 3 hours. After stirring for one-half hour, the standard work-up procedure afforded 483 grams (100%) of the desired 4-[(pyrid-4-yl)oxy]benzenesulfonyl chloride hydrochloride.

Workup

  1. additionadded dropwise over 3 hours

Sources & evidence

ORD record
ord-0f1f81267f4547be9dac4edfd506adcd
Source dataset
uspto-grants-2004_06
Patent number
US06750228B1

Reaction notes

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