Triethylamine → N-(4-phenylthiobenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazole carboxamide

HRID 2248377

Reaction equation

HRID 2248377 reaction equation
C(OCC)(=O)C.[C:7]1([S:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.CC1C=CC(OC2C=CC(CN[C:41]([C:43]3[N:47]([CH3:48])[N:46]=[C:45]([CH2:49][CH3:50])[C:44]=3[Cl:51])=[O:42])=CC=2)=CC=1>O>[C:7]1([S:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18][NH:19][C:41]([C:43]3[N:47]([CH3:48])[N:46]=[C:45]([CH2:49][CH3:50])[C:44]=3[Cl:51])=[O:42])=[CH:16][CH:15]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10110536TolfenpyradHCID 12842469[4-(Phenylsulfanyl)phenyl]methanamine

Product 1

HCID 15008488N-(4-phenylthiobenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazole carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 50 ml solution of ethyl acetate containing 3.50 g of 4-phenylthiobenzylamine and 2.2 g of triethylamine, was dropped 3.60 g of 4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxylic acid chloride synthesized in Example 2. After the completion of dropping, the mixture was stirred for 1.5 hours, poured into iced water and then extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of sodium carbonate, water and a saturated aqueous solution of sodium chloride. After drying over anhydrous sodium sulfate, the solution was concentrated under a reduced pressure. The residue was purified on silica gel column chromatography to obtain 4.70 g of the titled compound (No. 76) shown in Table 1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous solution of sodium carbonate, water
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. concentrationthe solution was concentrated under a reduced pressure
  5. customThe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-043a92cc036548b794a77392fa9feb9c
Source dataset
uspto-grants-1991_08
Patent number
US05039693

Linked notes

Loading…