Benzoyl Peroxide → HCID 88760946, compound

HRID 1155146Notes

Reaction equation

HRID 1155146 reaction equation
[H-].[Na+].[F:3][C:4]([F:39])([F:38])[C:5]1[CH:6]=[C:7]([CH2:15][NH:16][C:17](=[O:37])[CH2:18][C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)=[O:20])[CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12].C(OOC(=O)C1C=CC=CC=1)(=[O:47])C1C=CC=CC=1>CN(C)C=O>[F:3][C:4]([F:38])([F:39])[C:5]1[CH:6]=[C:7]([CH2:15][NH:16][C:17](=[O:37])[CH:18]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[C:25]([C:33]([F:34])([F:36])[F:35])[CH:24]=2)=[O:20])[OH:47])[CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 24758Sodium hydrideHCID 88759359HCID 88759359, compound

Product 1

HCID 88760946HCID 88760946, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of 0.515 g of sodium hydride (57% in mineral oil) in 10 ml of dry dimethylformamide, under a nitrogen atmosphere, add dropwise a solution of 6.0 g N,N'-bis-[3,4-bis-(trifluoromethyl)phenyl]methylmalonamide dissolved in 35 ml of dry dimethylformamide. Upon cessation of gas evolution, cool the resulting orange solution to about 0°-5° C. and add dropwise a solution of 2.8 g dibenzoyl peroxide in 30 ml of dry dimethylformamide. Stir the resulting white suspension for 16 hours at room temperature under a nitrogen atmosphere, quench with aqueous sodium bisulfite and extract with ether. Wash the ether extract with water, dry over sodium sulfate and remove the ether in vacuo. Chromatograph the residue on 200 g of acidic alumina and elute with hexane/methylene chloride (3:2) to separate the product from unreacted starting material. Recrystallize this material from 1:2 benzene/hexane to give the title compound [Rf =0.55 (tlc-silica gel, 7:1 chloroform/hexane].

Workup

  1. temperatureUpon cessation of gas evolution, cool the resulting orange solution to about 0°-5° C.
  2. customquench with aqueous sodium bisulfite
  3. extractionextract with ether
  4. washWash the ether
  5. extractionextract with water
  6. dry with materialdry over sodium sulfate
  7. customremove the ether in vacuo
  8. washChromatograph the residue on 200 g of acidic alumina and elute with hexane/methylene chloride (3:2)
  9. customto separate the product
  10. customRecrystallize this material from 1:2 benzene/hexane

Sources & evidence

ORD record
ord-2c3667062e424b00bb1a2e73ef445778
Source dataset
uspto-grants-1981_11
Patent number
US04299845

Reaction notes

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