Water → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine

HRID 579284Notes

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:24])[C:13]([NH:15][N:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>C1(C)C=CC=CC=1.CN(C)N>[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:24])[C:13]([N:15]([CH3:25])[N:16]=[CH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:14])[CH3:2]

Participants

Conditions

Temperature: 5 °C

Procedure

To a 50 mL volume three-necked flask, 1.0 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(phenylmethylidene)hydrazine ((40-a)-(14)-6), 3.5 ml of toluene and 629 mg of potassium carbonate were added and then, 9.1 mg of N,N-dimethylhydrazine solved in 2.3 ml of toluene and 577 mg of dimethyl sulfate were added thereto at 5° C. The mixture was stirred at 5° C. for 24 hours, 3 g of water was added thereto and the organic layer was removed. The aqueous layer was extracted with 3.5 ml of toluene two times. The organic layers were combined and concentrated under reduced pressure to give 1.037 g of a mixture (19:1 (GC area %)) of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine ((40-b)-(15)-5) and methyl 2-(2,6-diethyl-4-methylphenyl)-2-oxo-N-(phenylmethylidene)ethanehydrazonate (x-1)

Workup

customat 5° C
customthe organic layer was removed
extractionThe aqueous layer was extracted with 3.5 ml of toluene two times
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-48f81264690d43f8b6ea7ec73f62ba98
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040709B2

Reaction notes

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