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1-Chloro-4-nitrobenzene → 1-Methyl-4-(4-nitrophenoxy)-3,5-diphenyl-1H-pyrazole

HRID 436611
Notes
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Reaction equation

HRID 436611 reaction equation
[OH:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:4][N:5]([CH3:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].Cl[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1.[OH-].[Na+]>O.CN(C=O)C>[CH3:13][N:5]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:2]([O:1][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[C:3]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:4]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 12326421HCID 12326421, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 213980591-Methyl-4-(4-nitrophenoxy)-3,5-diphenyl-1H-pyrazoleYield 91.4%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-hydroxy-1-methyl-3,5-diphenylpyrazole (10 g, 0.04 mole), potassium t-butoxide (4.5, 0.04 mole) and dry DMF (150 ml) is stirred and heated to 60° C. The green fluorescent solution is cooled to room temperature and p-chloronitrobenzene (6.0 g, 0.038 mole) is added. The dark green solution is heated at 60° C for 24 hours and then poured into water, made alkaline with 1N sodium hydroxide and extracted with ether. The ether layer is separated, washed well with water, dried and stripped in vacuo to give a bright yellow solid 12.9 g (86.5%), m.p. 85° C to 110° C. The solid is chromatographed on silica gel with benzene to give a yellow crystalline solid 11.3 g, m.p. 74° C to 100° C. Recrystallization from methanol (185 ml) affords white crystals 5.5 g (37%) m.p. 120° C to 122° C.

Workup

  1. temperatureThe green fluorescent solution is cooled to room temperature
  2. temperatureThe dark green solution is heated at 60° C for 24 hours
  3. extractionextracted with ether
  4. customThe ether layer is separated
  5. washwashed well with water
  6. customdried

Sources & evidence

ORD record
ord-4f62de5c20db4953a164c0d4ada95afe
Source dataset
uspto-grants-1977_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04009277

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes