Toluene → HCID 33247581, compound

HRID 2307894Notes

Reaction equation

[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[H-].[Na+].[C:22]([NH:25][CH:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])(=[O:24])[CH3:23]>O.C(O)C>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][CH2:23][C:22]([NH:25][CH:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

25 g of 4-(tert-butyl)benzyl bromide, 50 ml of anhydrous toluene and 3.1 g of sodium hydride in 80% suspension in oil are added to a three-necked flask which is surmounted by a condenser, followed by 21.8 g of diethyl acetamidomalonate. The mixture is heated at 110° C. for 17 h. After it has been cooled down, 15 ml of absolute ethanol, then 15 ml of 50% ethanol and then 50 ml of water are added slowly to it using a dropping funnel. The organic phase is decanted and the aqueous phase is washed with 3 times 50 ml of diethyl ether. The organic phases are combined, washed with water and then dried over sodium sulphate. Following filtration and concentration under reduced pressure, the product is crystallized in petroleum ether in order to yield 25 g of diethyl 4-(tert-butyl)benzylacetamidomalonate in the form of a white solid which melts at 80° C.

Workup

customis surmounted by a condenser
temperatureAfter it has been cooled down
customThe organic phase is decanted
washthe aqueous phase is washed with 3 times 50 ml of diethyl ether
washwashed with water
dry with materialdried over sodium sulphate
filtrationfiltration and concentration under reduced pressure
customthe product is crystallized in petroleum ether in order

Sources & evidence

ORD record: ord-80a4640dc30a41da8f7addcd1cb9fdde
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833382B2

Reaction notes

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