Water → 1-(2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl)-1-methyl-2-(1-methylsulfanyl-2-propylidene)hydrazine

HRID 579219Notes

Reaction equation

HRID 579219 reaction equation
[CH3:1][NH:2][N:3]=[C:4]([CH3:8])[CH2:5][S:6][CH3:7].C(N(CC)CC)C.[CH2:16]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH2:25][CH3:26])[C:19]=1[C:27](=[O:31])[C:28](Cl)=[O:29])[CH3:17].O>C1(C)C=CC=CC=1>[CH2:16]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH2:25][CH3:26])[C:19]=1[C:27](=[O:31])[C:28]([N:2]([CH3:1])[N:3]=[C:4]([CH3:8])[CH2:5][S:6][CH3:7])=[O:29])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 569427122-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl chlorideHCID 764689571-Methyl-2-(1-methylsulfanyl-2-propylidene)hydrazine

Product 1

HCID 764689581-(2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl)-1-methyl-2-(1-methylsulfanyl-2-propylidene)hydrazineYield 86.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a 200 ml volume four-necked flask, 1-methyl-2-(1-methylsulfanyl-2-propylidene)hydrazine (5-0-1) (5.0 g), toluene (anhydrous) (9.6 g), and triethylamine (6.97 g) were added under a nitrogen atmosphere at room temperature. To the mixture, 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl chloride (6-a) (9.57 g) dissolved in toluene (28.8 g) was added dropwise at 0° C. over 2 hours, and stirred at room temperature for 2 hours. To the reaction mixture was added water (30 ml) at room temperature, and extracted with tert-butyl methyl ether. The organic layer was concentrated under reduced pressure to give 10.96 g of 1-(2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl)-1-methyl-2-(1-methylsulfanyl-2-propylidene)hydrazine ((4-4)-(1)-39).

Workup

  1. additionwas added dropwise at 0° C. over 2 hours
  2. extractionextracted with tert-butyl methyl ether
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-076008ffec6b43889b6b2bf960014682
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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