Toluene → HCID 33247581, compound

HRID 1934315Notes

Reaction equation

HRID 1934315 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

7

Reactant 4

HCID 1140TolueneHCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 33247581HCID 33247581, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

25 g of 4-tert-butylbenzyl bromide, 50 ml of anhydrous toluene and 3.1 g of sodium hydride as an 80% suspension in oil are added under a nitrogen atmosphere to a three-necked flask on which is mounted a condenser, followed by addition of 21.8 g of diethyl acetamidomalonate. The mixture is heated at 110° C. for 17 hours. After cooling, 15 ml of absolute ethanol, then 15 ml of 50% ethanol and then 50 ml of water are added slowly using a dropping funnel. The organic phase is separated out after settling has taken place 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. After filtering and concentrating under reduced pressure, the product is crystallized from petroleum ether to give 25 g of diethyl 4-(tert-butyl)benzylacetamidomalonate in the form of a white solid melting at 80° C.

Workup

  1. temperatureAfter cooling
  2. customThe organic phase is separated out after settling
  3. washthe aqueous phase is washed with 3 times 50 ml of diethyl ether
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtering
  7. concentrationconcentrating under reduced pressure
  8. customthe product is crystallized from petroleum ether

Sources & evidence

ORD record
ord-c33bee1d41cf43be8c3d37ff2c7bb1d1
Source dataset
uspto-grants-2002_05
Patent number
US06384014B1

Reaction notes

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