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O-Phenylenediamine → N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamide

HRID 1901048
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HRID 1901048 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C.[C:41]1([NH2:48])[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[NH2:47]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH2:47][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[NH:48][C:8](=[O:10])[C:7]1[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:13]([OH:14])=[C:12]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acid

생성물 1

HCID 23370116N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamide수율 32.4%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매

실험 절차

To a solution of 3,5-di-t-butyl-4-hydroxybenzoic acid (5.0 g) in methylene chloride (20 ml) was added dicyclohexylcarbodiimide (2.17 g) and the mixture was stirred overnight at room temperature. Subsequently, triethylamine (2.1 ml), 4-dimethylaminopyridine (0.37 g) and o-phenylenediamine (1.08 g) were added and the mixture was stirred overnight at room temperature. The insolubles was filtered off and the filtrate was concentrated to dryness. The residue was purified by a silica gel column chromatography (chloroform:ethyl acetate=20:1) and crystallized from diisopropyl ether to give N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamide (1.10 g, 32%).

후처리

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationThe insolubles was filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was purified by a silica gel column chromatography (chloroform:ethyl acetate=20:1)
  5. customcrystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-971f76d4d15449d0ab5c868d448dc7b5
출처 데이터셋
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05576335

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