Tributylamine → HCID 15136782, compound

HRID 893640Notes

Reaction equation

HRID 893640 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:4][N:3]=1.CS(O[CH:17]1[CH2:20][CH2:19][CH2:18]1)(=O)=O.C(N(CCCC)CCCC)CCC>C(OCC)C>[CH:20]1([CH2:17][N:4]2[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:6][C:2]([CH3:1])=[N:3]2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 15137785HCID 15137785, compoundHCID 178469061HCID 178469061, compound

Product 1

HCID 15136782HCID 15136782, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture comprising 2.1 g of ethyl 3-methyl-1H-pyrazole-5-carboxylate, 2.1 g of cyclobutyl methanesulfonate and 2.6 g of tri-n-butylamine was allowed to react at 110 ° C. for three hours without using any solvent. Then the reaction mixture was allowed to cool and diethyl ether was added thereto. The obtained mixture was successively washed with 1 N hydrochloric acid, an aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by column chromatography (eluent: hexane : ethyl acetate=14 : 1). Thus 0.5 g of the aimed ethyl 1-cyclobutyl-3-methyl-1H-pyrazole-5-carboxylate (compound No. 1001) (yield: 17.6 %) and 1.54 g of ethyl 1-cyclopropylmethyl-3-methyl-1H-pyrazole-5-carboxylate(yield: 54.3 %) were obtained.

Workup

  1. customto react at 110 ° C. for three hours
  2. temperatureto cool
  3. washThe obtained mixture was successively washed with 1 N hydrochloric acid
  4. dry with materialan aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by column chromatography (eluent: hexane : ethyl acetate=14 : 1)

Sources & evidence

ORD record
ord-beaf1fe8b664403cb9fe91a97d33f586
Source dataset
uspto-grants-1992_06
Patent number
US05126362

Reaction notes

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