Pyridine → 5-Chloro-2-(2,2-difluoroacetamido)benzenesulphonamide

HRID 915743

Reaction equation

HRID 915743 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].N1C=CC=CC=1.[F:19][CH:20]([F:24])[C:21](Cl)=[O:22]>O1CCOCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:21](=[O:22])[CH:20]([F:24])[F:19])=[C:3]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27368902,2-Difluoroacetyl chlorideHCID 122955502-Amino-5-chlorobenzenesulphonamide

Product 1

HCID 231042325-Chloro-2-(2,2-difluoroacetamido)benzenesulphonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 1 g of 2-amino-5-chlorobenzenesulphonamide (obtained in accordance with J. Chem. Soc. Perkin I 1979, 1043-1047) dissolved in 4 ml of dioxane there are added, in the cold state (+5° C.), 0.6 ml of pyridine and 0.6 ml of difluoroacetic acid chloride. The flask is hermetically closed immediately and subjected to vigorous stirring at ambient temperature for 10 minutes. The solvents are then removed under reduced pressure. The solid residue is taken up in water (12 ml), and the insoluble material is collected by filtration, washed with water and dried to yield the expected compound.

Workup

  1. customThe flask is hermetically closed immediately
  2. customThe solvents are then removed under reduced pressure
  3. filtrationthe insoluble material is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9d2c3e9d62a24924ad2245c0bdc30ea4
Source dataset
uspto-grants-2007_09
Patent number
US07268129B2

Linked notes

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