4-Methylpyrazole → HCID 68787041, compound

HRID 1519960Notes

Reaction equation

HRID 1519960 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:9]=[N:10][NH:11][CH:12]=1.Cl[C:14]1[S:15][CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20]>CN(C=O)C.[Cl-].[Na+].O>[CH3:7][C:8]1[CH:9]=[N:10][N:11]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[N+:19]([O-:21])=[O:20])[CH:12]=1

Participants

6

Reactant 3

HCID 34064-MethylpyrazoleHCID 2201862-Chloro-3-nitrothiopheneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68787041HCID 68787041, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium tert-butoxide (2.78 g, 24.8 mmol) and 4-methyl-1H-pyrazole (3.0 ml g, 37.3 mmol) in DMF (50 ml) was stirred for 30 min. 2-chloro-3-nitrothiophene (3.08 g, 18.7 mmol) was added and the solution was placed into a preheated oil bath at 100° C. After stirring for 1 h, the solution was diluted with brine and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was flash chromatographed with 9:1, 4:1, 7:3, 3:2, and 1:1 hexane:ethyl acetate as the eluant to yield 4-methyl-1-(3-nitrothiophen-2-yl)-1H-pyrazole. Method [1] Retention time 1.80 min by HPLC (MH+ 210).

Workup

  1. customthe solution was placed into a preheated oil bath at 100° C
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed with 9:1, 4:1, 7:3, 3:2, and 1:1 hexane

Sources & evidence

ORD record
ord-3dbfd5cb60f3481999db517ab9a0d3a9
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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