Hydrochloric Acid → N-(4-methylsulfonylphenylsulfonyl)-2-chloroisonicotinamide

HRID 2308611Notes

Reaction equation

HRID 2308611 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19](Cl)=[O:20].Cl.CCCCCC.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][N:24]=[C:16]([Cl:15])[CH:17]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1203134-(Methanesulfonyl)benzene-1-sulfonamideHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 13924304N-(4-methylsulfonylphenylsulfonyl)-2-chloroisonicotinamideYield 74.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.3 g (0.01 mol) of 4-methylsulfonylbenzenesulfonamide were dissolved in 20 ml of pyridine, and added dropwise by 1.7 g (0.01 mol) of 2-chloroisonicotinoyl chloride at room temperature, followed by agitation for 2 hrs. at the same temperature. After acidified by adding aqueous hydrochloric acid, the precipitate was extracted by ethyl acetate. The organic layer obtained was dried and then concentrated to precipitate crude crystals, which were recrystallized by n-hexane/ethyl acetate to 2.8 g (yield: 74.7%) of N-(4-methylsulfonylphenylsulfonyl)-2-chloroisonicotinamide as white crystals.

Workup

  1. extractionthe precipitate was extracted by ethyl acetate
  2. customThe organic layer obtained
  3. customwas dried
  4. concentrationconcentrated
  5. customto precipitate crude crystals, which

Sources & evidence

ORD record
ord-e97899d99d384486be14ddeb173e2a60
Source dataset
uspto-grants-1987_09
Patent number
US04690934

Reaction notes

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