Hydrochloric Acid → N-(4-chloro-2-trifluoromethylphenylsulfonyl)-2-chloroisonicotinamide

HRID 2308612Notes

Reaction equation

HRID 2308612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][N:25]=1)[C:20](Cl)=[O:21].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][N:25]=[C:17]([Cl:16])[CH:18]=2)(=[O:10])=[O:9])=[C:4]([C:12]([F:15])([F:13])[F:14])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 75098844-Chloro-2-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 13924313N-(4-chloro-2-trifluoromethylphenylsulfonyl)-2-chloroisonicotinamideYield 85.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.6 g (0.01 mol) of 4-chloro-2-trifluoromethylbenzenesulfonamide were dissolved in 20 ml of pyridine, 2-chloroisonicotinoyl chloride was added dropwise at room temperature. Agitation was then continued for 2 hr. at the same temperature. The reaction mixture was acidified by adding aqueous hydrochloric acid, and the precipitate thus formed was extracted by ethyl acetate. The organic layer obtained was dried and then concentrated to precipitate crude crystals, which were recrystallized by solvent mixture of n-hexane and ethyl acetate to produce 3.4 g (yield: 85.1%) of N-(4-chloro-2-trifluoromethylphenylsulfonyl)-2-chloroisonicotinamide as white crystals.

Workup

  1. customthe precipitate thus formed
  2. extractionwas extracted by ethyl acetate
  3. customThe organic layer obtained
  4. customwas dried
  5. concentrationconcentrated
  6. customto precipitate crude crystals, which
  7. customwere recrystallized by solvent mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-59c44b8f7cb94e3284cd574f85f29542
Source dataset
uspto-grants-1987_09
Patent number
US04690934

Reaction notes

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