Ethanol → HCID 23114553, compound

HRID 2080488Notes

Reaction equation

HRID 2080488 reaction equation
C(O)C.Cl[C:5]1[CH:10]=[C:9]([CH:11]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[C:8]([Cl:30])=[CH:7][N:6]=1.O.[NH2:32][NH2:33]>CCCCCC>[Cl:30][C:8]1[C:9]([CH:11]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])=[CH:10][C:5]([NH:32][NH2:33])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 23114596HCID 23114596, compound

Product 1

HCID 23114553HCID 23114553, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To an ethanol (10 ml) solution of the 2,5-dichloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridine (524 mg, 1.17 mmol) obtained in Example 57 was added hydrazine monohydrate (2 ml). The resulting mixture was heated under reflux for 3 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=1:1) eluate was concentrated under reduced pressure to afford a pale yellow oil. To the resulting oil was added hexane-ether and the solid thus precipitated was collected by filtration to give the title compound (95 mg, 0.214 mmol, 18%) as a white powder.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue thus obtained
  5. concentrationethyl acetate (=1:1) eluate was concentrated under reduced pressure
  6. customto afford a pale yellow oil
  7. customthe solid thus precipitated
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-daf013c410184d72bf647b64499a4f06
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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