N-Phenylhydroxylamine → N-Hydroxy-N-phenyl-4-(4-phenylbutyl)benzamide

HRID 365048Notes

Reaction equation

HRID 365048 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[C:26]1([NH:32][OH:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C1C=CC=CC=1.C1COCC1.C1COCC1.O.CCOC(C)=O.CN(C=O)C>[OH:33][N:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:19][CH:18]=1

Participants

10

Reactant 4

HCID 7518N-PhenylhydroxylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3086974-(4-Phenylbutyl)benzoic acid

Product 1

HCID 20238920N-Hydroxy-N-phenyl-4-(4-phenylbutyl)benzamide

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirring solution of 4-(4-phenylbutyl)benzoic acid (prepared as described in Example 173) (370 mg, 1.45 mmol) in 10 ml of dry benzene under argon, was added oxalyl chloride (0.14 ml, 2.0 eq.). To this solution was added DMF dropwise in 10 minute intervals, until no gas was evolved and the solution turned slightly cloudy (2 drops). The mixture was stirred for 1 hour, then reduced on the rotovap without heating. The crude product was dissolved in 5 ml of THF and added dropwise to a 0° C. solution of N-phenyl hydroxylamine (317 mg, 2.0 eq.) in 20 ml of THF:H2O (1:1) with triethylamine (0.41 ml, 2.0 eq.). The solution was stirred for 1 hour at 0° C., then allowed to warm to room temperature and stir overnight. The reaction mixture was diluted with EtOAc and the organic layer was washed with H2O, 1N HCl (2×), and brine, then dried over anhydrous MgSO4. Concentration in vacuo gave a white solid which was triturated with hexane to remove a yellow impurity and recrystallized from hot hexane/EtOAc, to give title product, 256 mg (51%).

Workup

  1. temperaturewithout heating
  2. stirringThe solution was stirred for 1 hour at 0° C.
  3. stirringstir overnight
  4. washthe organic layer was washed with H2O, 1N HCl (2×), and brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationConcentration in vacuo
  7. customgave a white solid which
  8. customwas triturated with hexane
  9. customto remove a yellow impurity
  10. customrecrystallized from hot hexane/EtOAc

Sources & evidence

ORD record
ord-cf7b81eec30c44d59878c931828e81f2
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

Loading…