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

HRID 1087207Notes

Reaction equation

HRID 1087207 reaction equation
CS(NC1C=CC=CC=1)(=O)=O.[C:12]([C:15]1[CH:25]=[CH:24][C:18]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:17]([S:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[F:34])[CH:16]=1)(=O)[CH3:13].Cl.[NH2:36][NH:37][C:38]([NH2:40])=[O:39].N1C=CC=CC=1>C(O)C>[F:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]=1[S:26][C:17]1[CH:16]=[C:15]([C:12](=[N:36][NH:37][C:38]([NH2:40])=[O:39])[CH3:13])[CH:25]=[CH:24][C:18]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11236Semicarbazide hydrochlorideHCID 198177324'-Acetyl-2'-(2,4-difluorophenylthio)methanesulfonanilide methanesulfonanilide

Product 1

HCID 540195573'-(2,4-Difluorophenylthio)-4'-methanesulfonamidoacetophenone semicarbazoneYield 101.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4'-acetyl-2'-(2,4-difluorophenylthio)methanesulfonanilide methanesulfonanilide (1.16 g), semicarbazide hydrochloride (0.4 g), and pyridine (0.29 ml) in ethanol (15 ml) was stirred and refluxed for 2 hours. The mixture was concentrated under reduced pressure. The residue was triturated with water, filtered, washed with water, and recrystallized from methanol to give a powder of 3'-(2,4-difluorophenylthio)-4'-methanesulfonamidoacetophenone semicarbazone (0.92 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. washwashed with water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-03e55ede65b244c1a54c8999ddb97567
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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