Tetrahydrofuran → 1-[2-(1,3,5-Triethylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine

HRID 335433Notes

Reaction equation

[CH3:1][NH:2][N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7].O1CCCC1.C(N(CC)CC)C.[CH2:23]([C:25]1([C:35](=[O:39])[C:36](Cl)=[O:37])[CH:30]=[C:29]([CH2:31][CH3:32])[CH:28]=[C:27]([CH2:33][CH3:34])[CH2:26]1)[CH3:24]>CCCCCC>[CH2:23]([C:25]1([C:35](=[O:39])[C:36]([N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])=[O:37])[CH:30]=[C:29]([CH2:31][CH3:32])[CH:28]=[C:27]([CH2:33][CH3:34])[CH2:26]1)[CH3:24]

Participants

Conditions

Temperature: 1 °C

Procedure

To a 3 L volume four-necked flask, 1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine (5-2-1) (116.0 g), tetrahydrofuran (anhydrous) (600 ml), and triethylamine (98.5 ml) were added under a nitrogen atmosphere, and cooled to about 1° C. To the mixture, 2-(1,3,5-triethylphenyl)-2-oxoacetyl chloride (6-b) (178.5 g) was added dropwise, and stirred at 0° C. for 1 hour. The reaction mixture was added dropwise to hexane (3 L) at room temperature, and stirred for 1 hour. The precipitated solids were collected by filtration, washed with hexane (0.5 L×2) and water (0.5 L×6), and dried under reduced pressure to give 200.9 g of 1-[2-(1,3,5-triethylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(1)-40).

Workup

stirringstirred for 1 hour
filtrationThe precipitated solids were collected by filtration
washwashed with hexane (0.5 L×2) and water (0.5 L×6)
customdried under reduced pressure

Sources & evidence

ORD record: ord-449d16c045054f159f41c4c5f9d38e5a
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

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