1-(3-Cyano-4-methoxyphenyl)-5-[4-(methylthio)phenyl]-2-pyrazoline-3-amine → 1-(3-Cyano-4-methoxyphenyl)-5-[4-(methylthio)phenyl]pyrazole-3-amine

HRID 429324Notes

Reaction equation

HRID 429324 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=3)[CH2:14][C:13]([NH2:24])=[N:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])#[N:2]>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[C:1]([C:3]1[CH:4]=[C:5]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=3)=[CH:14][C:13]([NH2:24])=[N:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])#[N:2]

Participants

4

Reactant 1

HCID 183554041-(3-Cyano-4-methoxyphenyl)-5-[4-(methylthio)phenyl]-2-pyrazoline-3-amine

Product 1

HCID 183553791-(3-Cyano-4-methoxyphenyl)-5-[4-(methylthio)phenyl]pyrazole-3-amineYield 27.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-(3-cyano-4-methoxyphenyl)-5-[4-(methylthio)phenyl]-2-pyrazoline-3-amine (4.0 g) and manganese(IV) oxide (6.0 g) in toluene (100 ml) was stirred at ambient temperature for 8 hours. The insoluble material was filtered and washed with ethyl acetate. The resulting solution was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel eluting with a mixture of acetone and dichloromethane (1:1) to give partially purified 1-(3-cyano-4-methoxyphenyl)-5-[4-(methylthio)phenyl]pyrazole-3-amine (1.1 g).

Workup

  1. filtrationThe insoluble material was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe resulting solution was concentrated under reduced pressure
  4. additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of acetone and dichloromethane (1:1)

Sources & evidence

ORD record
ord-8159d657b03644d0bb0d62ffacccb004
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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