Toluene → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine

HRID 335408Notes

Reaction equation

[CH3:1][NH:2][N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7].C1(C)C=CC=CC=1.C(#N)C.[CH2:21]([C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH2:30][CH3:31])[C:24]=1[C:32](=[O:36])[C:33](Cl)=[O:34])[CH3:22]>O.C(N(CC)CC)C>[CH2:21]([C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH2:30][CH3:31])[C:24]=1[C:32](=[O:36])[C:33]([N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])=[O:34])[CH3:22]

Participants

Conditions

Temperature: 1 °C

Procedure

To a 100 ml volume four-necked flask, 1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine (5-2-1) (2.51 g), toluene (anhydrous) (10 ml), acetonitrile (anhydrous) (4.0 ml), and triethylamine (4.0 ml) were added under a nitrogen atmosphere and cooled to about 1° C. To the mixture, 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl chloride (6-a) (3.44 g) dissolved in toluene1 (5 ml) was added dropwise over 1 hour, followed by the mixture was stirred at 0° C. for 1.5 hours. Water (30 ml) was added thereto at room temperature, and then the mixture was extracted with tert-butyl methyl ether. The organic layer was concentrated under reduced pressure to give 5.09 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(1)-39).

Workup

additionwas added dropwise over 1 hour
extractionat room temperature, and then the mixture was extracted with tert-butyl methyl ether
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-2ebd48ab3293488880f19958c721a71a
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

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