Ethyl Acetate → HCID 23174225, compound

HRID 654784Notes

Reaction equation

HRID 654784 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:21]([N:23]([CH3:25])[CH3:24])=O)=[N:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].C(OCC)(=O)C>CCOCC.C1C=CC=CC=1>[CH3:24][N:23]([CH2:21][C:10]1[CH:11]=[C:12]([C:13]2[CH:14]=[CH:15][C:16]([S:19][CH3:20])=[CH:17][CH:18]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]=1)[CH3:25]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19886178HCID 19886178, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 23174225HCID 23174225, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-N,N-dimethyl-5-[4-(methylthio)phenyl)pyrazole-3-carboxamide (1.6 g) and lithium aluminum hydride (0.34 g) in ether (8.5 ml) and benzene (13 ml) was stirred and refluxed for 2 hours. 4N Sodium hydroxide (10 ml) was added dropwise and ethyl acetate (20 ml) was added to the mixture. The insoluble was filtered and the filtrate was separated. The organic layer was washed with water, dried and concentrated. The residue (1.2 g) was purified by column chromatography on silica gel (30 g) eluting with a mixture of ethyl acetate and methanol (5:1) to give a pale brown oil of 3-(N,N-dimethylaminomethyl)-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazole (0.69 g).

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe insoluble was filtered
  3. customthe filtrate was separated
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue (1.2 g) was purified by column chromatography on silica gel (30 g)
  8. washeluting with a mixture of ethyl acetate and methanol (5:1)

Sources & evidence

ORD record
ord-a7943dad9f1b480c981ce762333287e4
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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