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

HRID 550546Notes

Reaction equation

HRID 550546 reaction equation
[CH3:1][C:2]([CH3:10])([CH2:7][CH:8]=[CH2:9])[C:3]([NH:5][NH2:6])=O.C([O-])([O-])=O.[K+].[K+].Cl.[CH3:18][NH:19][C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=NC>CN1C(=O)CCC1>[CH3:1][C:2]([C:3]1[N:19]([CH3:18])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:6][N:5]=1)([CH3:10])[CH2:7][CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12382386N,N'-dimethylbenzenecarboximidamide hydrochlorideHCID 576918522,2-Dimethyl-4-pentenohydrazide

Product 1

HCID 576918753-(1,1-dimethyl-3-buten-1-yl)-4-methyl-5-phenyl-4H-1,2,4-triazoleYield 32.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
240 °C

Procedure

To a solution of 2,2-dimethyl-4-pentenohydrazide (360 mg) in NMP(2.5 ml) were added K2CO3 (348 mg) and N,N′-dimethylbenzenecarboximidamide hydrochloride (463 mmol). The solution was heated to the microwave at 240° C. for 30 minutes. Volatiles were evaporated in vacuo, the crude dissolved in DCM, washed with water and dried over Na2SO4. After filtration and concentration to dryness in vacuo, the crude was purified by column chromatography (DCM:MeOH=98 to 2) to give 196 mg of the title compound. MS (m/z): 242[MH]+.

Workup

  1. customVolatiles were evaporated in vacuo
  2. dissolutionthe crude dissolved in DCM
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration to dryness in vacuo
  6. customthe crude was purified by column chromatography (DCM:MeOH=98 to 2)

Sources & evidence

ORD record
ord-b5aa1ae7db544f1593f7c7c18c27cefc
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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