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

HRID 1768669Notes

Reaction equation

HRID 1768669 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].[H-].[K+].[H][H].[CH3:20][C:21]([CH3:34])([CH3:33])[C:22]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)=[O:23]>O1CCCC1.CCCCCC>[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:11][C:28](=[O:29])[C:27]2[CH:26]=[CH:25][C:24]([C:22](=[O:23])[C:21]([CH3:20])([CH3:33])[CH3:34])=[CH:32][CH:31]=2)=[O:10])=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 82127Potassium hydrideHCID 105362344-(2,2-Dimethyl-1-oxopropyl)-benzamideHCID 11806342Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-HCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

4.2 grams (20.5 mmoles) of 4-(2,2-dimethyl-1-oxopropyl) benzamide is dissolved in 100 milliliters of dry tetrahydrofuran. The solution is cooled to 0° C., and 3.7 grams (22.6 mmoles) of potassium hydride (from a 24.5% mixture in mineral oil) which has been washed free of oil with hexane, is added. After hydrogen evolution has ceased, (approximately 2 hours), a solution of 4.6 grams (20.5 mmoles) of 4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride in 20 milliliters of dry tetrahydrofuran is added dropwise at 0° C. When addition is complete, the reaction mixture is concentrated in vacuo, and the residue is then dissolved in methylene dichloride and filtered to remove solids. The filtrate is purified by flash chromatography (3 inch column and 0.3% then 1% methanol/methylene chloride to elute) and crystallized from diethyl ether to yield the title product (m.p. 131°-132° C.).

Workup

  1. additionis added
  2. custom, (approximately 2 hours),
  3. additionis added dropwise at 0° C
  4. additionWhen addition
  5. concentrationthe reaction mixture is concentrated in vacuo
  6. dissolutionthe residue is then dissolved in methylene dichloride
  7. filtrationfiltered
  8. customto remove solids
  9. customThe filtrate is purified by flash chromatography (3 inch column and 0.3%
  10. wash1% methanol/methylene chloride to elute) and
  11. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-c881b126b3004ca1929902fc5ee5105c
Source dataset
uspto-grants-1995_01
Patent number
US05378728

Reaction notes

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