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2-Amino-4-methylphenol → 2'-Hydroxy-5'-methyl-4-(4-phenylbutoxy)benzanilide

HRID 847278
ノート
印刷プレビュー

反応式

HRID 847278 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[OH:29]>CN(C)C=O.C(Cl)Cl.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1>[OH:29][C:23]1[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=1[NH:21][C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:20][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 72642-Amino-4-methylphenolHCID 110438254-(4-Phenylbutoxy)benzoic Acid

生成物 1

HCID 151065462'-Hydroxy-5'-methyl-4-(4-phenylbutoxy)benzanilide収率 100.8%

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane
溶媒
2 回
HCID 65578Oxalyl chloride溶媒

実験手順

One drop of N,N-dimethylformamide was added to a solution of 1 g of p-(4-phenylbutoxy)benzoic acid in 5 ml of methylene chloride and 2 ml of oxalyl chloride was added to the mixture at -30° C. or lower. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure to obtain crude p-(4-phenylbutoxy)benzoyl chloride. This substance was dissolved in 5 ml of methylene chloride and the resulting solution was added to a solution of 1 g of 2-amino-4-methylphenol in 5 ml of pyridine under ice cooling followed by stirring at room temperature for 3 hours. The reaction mixture was poured into conc. hydrochloric acid-ice and then extracted with ethyl acetate. The extract was washed subsequently with water, an aqueous solution of sodium hydrogen carbonate and again water. After drying over anhydrous magnesium sulfate, the system was concentrated under reduced pressure to obtain 1.4 g of 2'-hydroxy-5'-methyl-4-(4-phenylbutoxy)benzanilide. Melting point: 138°~140 ° C.

後処理

  1. additionwas added to the mixture at -30° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto obtain crude p-(4-phenylbutoxy)benzoyl chloride
  4. stirringby stirring at room temperature for 3 hours
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed subsequently with water
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. concentrationthe system was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-6e6167f2e9b54cc987d2459697599245
出典データセット
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05140046

反応ノート

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