Pyridine → 4'-Amino-3'-chloro-5'-(2,4-difluorophenylthio)acetophenone

HRID 1087203Notes

Reaction equation

HRID 1087203 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].N1C=CC=CC=1.[Cl-:26].[Cl-].IC1C=CC=CC=1>O1CCCC1>[NH2:1][C:2]1[C:3]([S:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[CH:6][C:7]=1[Cl:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10062143HCID 10062143, compoundHCID 13166207CID 13166207

Product 1

HCID 198177434'-Amino-3'-chloro-5'-(2,4-difluorophenylthio)acetophenoneYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4'-amino-3'-(2,4-difluorophenylthio)acetophenone (2 g), pyridine (0.623 g) and iodobenzene dichloride (2.7 g) in tetrahydrofuran (20 ml) was stirred for 1.5 hours at 0° to 5° C. The mixture was concentrated to dryness. The residue was dissolved in ethyl acetate, washed with water and an aqueous solution of sodium hydrogensulfite successively, dried, and evaporated. The solid residue was washed with a mixture of hexane and ethanol to give 4'-amino-3'-chloro-5'-(2,4-difluorophenylthio)acetophenone (1.7 g).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialan aqueous solution of sodium hydrogensulfite successively, dried
  5. customevaporated
  6. washThe solid residue was washed with a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-b5fa905a119a451ca92cabc855ccc615
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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