Pyridine → HCID 19850891, compound

HRID 1607694Notes

Reaction equation

HRID 1607694 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:7]([O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[CH:6]=1)=[O:4].[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl:31]CCl>Cl>[Cl-:31].[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[O:16][C:7]1[CH:6]=[C:5]([CH:15]=[CH:14][C:8]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[C:3]([CH2:2][N+:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6344DichloromethaneHCID 10319939HCID 10319939, compound

Product 1

HCID 19850891HCID 19850891, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4'-bromoacetyl-2'-(2,4-difluorophenoxy)methanesulfonanilide (2.5 g) and pyridine (526 mg) in dichloromethane (20 ml) was refluxed for 4 hours. The mixture was concentrated, and the residue was dissolved in water and washed with ethyl acetate. To the aqueous layer was added sodium bicarbonate, giving an amorphous powder. The powder 0.76 g) was dissolved in an ethanolic solution of hydrogen chloride. The residue obtained by evaporation of the solution was crystallized with ethyl acetate to give a powder of 1-[3-(2,4-difluorophenoxy)-4-(methanesulfonamido)benzoylmethyl]pyridinium chloride (0.75 g).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. washwashed with ethyl acetate
  4. additionTo the aqueous layer was added sodium bicarbonate
  5. customgiving an amorphous powder
  6. customThe residue obtained by evaporation of the solution
  7. customwas crystallized with ethyl acetate

Sources & evidence

ORD record
ord-31ff7233b0674158b704edba2b8a0c19
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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