Acetic Acid → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-(1-methylsulfanyl-2-propylidene)hydrazine

HRID 335413

Reaction equation

HRID 335413 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:17])[C:13]([NH:15][NH2:16])=[O:14])[CH3:2].O1CCCC1.C(O)(=O)C.[CH3:27][S:28][CH2:29][C:30](=O)[CH3:31]>O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:17])[C:13]([NH:15][N:16]=[C:30]([CH3:31])[CH2:29][S:28][CH3:27])=[O:14])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 64307131-Methylthio-2-propanoneHCID 569428732-(2,6-Diethyl-4-methylphenyl)-2-oxoacetohydrazide

Product 1

HCID 866893451-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-(1-methylsulfanyl-2-propylidene)hydrazineYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 200 ml volume four-necked flask, 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetohydrazine ((12-1)-(11)-39) (6.44 g), tetrahydrofuran (72 ml), and acetic acid (1.65 g) were added under a nitrogen atmosphere. 1-methylsulfanyl-2-propanone (7-0-1) (3.12 g) was added at room temperature, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added water (30 ml), and extracted with tert-butyl methyl ether. The organic layer was concentrated under reduced pressure to give 7.17 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(1-methylsulfanyl-2-propylidene)hydrazine ((4-4)-(8)-39).

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f22862d887c94aacbe6b1121c774211b
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Linked notes

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