Pyridine → 3'-(2,4-Difluorophenoxy)-4'-methanesulfonamidoacetophenone semicarbazone

HRID 1607690Notes

Reaction equation

HRID 1607690 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:5]=1)(=O)[CH3:2].Cl.[NH2:25][NH:26][C:27]([NH2:29])=[O:28].N1C=CC=CC=1>C(O)C>[F:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[O:15][C:6]1[CH:5]=[C:4]([C:1](=[N:25][NH:26][C:27]([NH2:29])=[O:28])[CH3:2])[CH:14]=[CH:13][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11236Semicarbazide hydrochlorideHCID 164009FK 3311

Product 1

HCID 543913703'-(2,4-Difluorophenoxy)-4'-methanesulfonamidoacetophenone semicarbazoneYield 62.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4'-acetyl-2'-(2,4-difluorophenoxy)methanesulfonanilide (1.5 g), semicarbazide hydrochloride (0.5 g), and pyridine (0.35 g) in ethanol (20 ml) was stirred and refluxed for 2 hours. The mixture was concentrated under reduced pressure. The residue was triturated with water, filtered, and recrystallized from methanol to give a powder of 3'-(2,4-difluorophenoxy)-4'-methanesulfonamidoacetophenone semicarbazone (1.1 g).

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was triturated with water
  4. filtrationfiltered
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-695207a05b3a4277b84af2cd87e22db6
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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