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

HRID 365048ノート

反応式

HRID 365048 の反応式
[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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 241Benzene溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-cf7b81eec30c44d59878c931828e81f2
出典データセット
uspto-grants-1986_08
特許番号
US04607053

反応ノート

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