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

HRID 982217
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인쇄 미리보기

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HRID 982217 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 1049Pyridine용매HCID 6344
Dichloromethane
용매
2회
HCID 65578Oxalyl chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c0a13a5b193e4057893b9351a46c16b2
출처 데이터셋
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04994479

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