4-(2,2-Dimethyl-1-oxopropyl)-benzamide → 4-(2,2-dimethyl-1-oxopropyl)-N-[4-(2,2-dimethyl-1-oxopropyl)-benzoyl]benzamide

HRID 1768676Notes

Reaction equation

HRID 1768676 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][CH:6]=1)=[O:4].[C:16]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:11][C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([C:16](=[O:21])[C:17]([CH3:18])([CH3:19])[CH3:20])=[CH:30][CH:29]=2)=[O:10])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 105362344-(2,2-Dimethyl-1-oxopropyl)-benzamideHCID 11806342Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-

Product 1

HCID 98007244-(2,2-dimethyl-1-oxopropyl)-N-[4-(2,2-dimethyl-1-oxopropyl)-benzoyl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 12.3 grams (60 mmol) of 4-(2,2-dimethyl-1-oxo-propyl)-benzamide dissolved in 450 ml of THF is chilled to 5° C.; and 20.6 grams of 35% potassium hydride in oil washed twice with hexane is added as a suspension in hexane. The resulting mixture is stirred for hours at 5° C. A solution of 13.8 grams (61.4 mmol) of p-pivaloyl-benzoyl chloride dissolved in 100 ml of THF is added with stirring over a period of 21/2 hours at 5° C. Sitrring is continued for an additional hour at this temperature, following which the mixture is stirred into 500 ml of an ice-cold saturated NH4Cl solution. The liquid phases are separated, and the aqueous phase is extracted with t-butyl methyl ether. The combined organic layers are washed with saturated sodium chloride solution, separated, and dried over magnesium sulfate. After filtering off the magnesium sulfate, the filtrate is evaporated to a solid, and the crude product is partially purified by chromatography on silica with CHCl3 eluant. The resulting product is twice crystallized from isopropyl alcohol and then from methylene chloride/t-butyl methyl ether, yielding the title product (mp 132°-134° C.).

Workup

  1. washand 20.6 grams of 35% potassium hydride in oil washed twice with hexane
  2. additionis added as a suspension in hexane
  3. additionis added
  4. waitSitrring is continued for an additional hour at this temperature
  5. customThe liquid phases are separated
  6. extractionthe aqueous phase is extracted with t-butyl methyl ether
  7. washThe combined organic layers are washed with saturated sodium chloride solution
  8. customseparated
  9. dry with materialdried over magnesium sulfate
  10. filtrationAfter filtering off the magnesium sulfate
  11. customthe filtrate is evaporated to a solid
  12. customthe crude product is partially purified by chromatography on silica with CHCl3 eluant
  13. customThe resulting product is twice crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-3b7672552f594432b81d5abef6b1a85a
Source dataset
uspto-grants-1995_01
Patent number
US05378728

Reaction notes

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