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Potassium Carbonate → 3-(1,1-difluoro-4-penten-1-yl)-4-methyl-5-phenyl-4H-1,2,4-triazole

HRID 550548
Notes
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Reaction equation

HRID 550548 reaction equation
[F:1][C:2]([F:11])([CH2:7][CH2:8][CH:9]=[CH2:10])[C:3]([NH:5][NH2:6])=O.C([O-])([O-])=O.[K+].[K+].Cl.[CH3:19][NH:20][C:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=NC>CO>[F:1][C:2]([C:3]1[N:20]([CH3:19])[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:6][N:5]=1)([F:11])[CH2:7][CH2:8][CH:9]=[CH2:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12382386N,N'-dimethylbenzenecarboximidamide hydrochlorideHCID 576918935-Hexenoic acid, 2,2-difluoro-, hydrazide

Product 1

HCID 576918883-(1,1-difluoro-4-penten-1-yl)-4-methyl-5-phenyl-4H-1,2,4-triazoleYield 10.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2-difluoro-5-hexenohydrazide (275 mg) in MeOH (8 ml) were added K2CO3 (232 mg) and N,N′-dimethylbenzenecarboximidamide hydrochloride (309 mmol). The solution was heated at reflux for 3 days. Volatiles were evaporated in vacuo and the crude was purified by column chromatography (DCM:MeOH=95 to 5) to give 45 mg of the title compound. MS (m/z): 264[MH]+.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 days
  3. customVolatiles were evaporated in vacuo
  4. customthe crude was purified by column chromatography (DCM:MeOH=95 to 5)

Sources & evidence

ORD record
ord-cc55b856928d40e7ac7cf21c40ad1c12
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07947683B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes