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Gallic Acid → 3,4,5-trihydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamide

HRID 393841
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HRID 393841 반응식
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.Cl.[N+:14]([C:17]1(OCC)[CH:22]=[CH:21][C:20](N)=[CH:19][CH2:18]1)([O-:16])=[O:15].Cl.C[N:29](C)[CH2:30][CH2:31]CN=C=NCC.C(N(CC)CC)C>ClCCl.O.CN(C=O)C>[OH:9][C:8]1[CH:10]=[C:2]([CH:3]=[C:4]([OH:5])[C:6]=1[OH:7])[C:1]([NH:29][CH2:30][CH2:31][C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=1)=[O:12]
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참가 물질

8

반응물 4

HCID 370Gallic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 690034264-Nitrophenetylamine hydrochloride

생성물 1

HCID 219187493,4,5-trihydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamide수율 42%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매

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온도
20 °C

실험 절차

2 g (11.5 mmoles) of gallic acid, 2.5 g (11.5 mmoles) of 4-nitrophenetylamine hydrochloride, 1.8 g (11.5 mmoles) of hydrated 1-hydroxybenzotriazole, 2.25 g (11.5 mmoles) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.3 ml (23 mmoles) of triethylamine are introduced into a 100 ml flask containing 30 ml of anhydrous DMF. The orange-coloured solution obtained is agitated at 20° C. for 20 hours and diluted in a mixture of dichloromethane (50 ml) and water (30 ml). After decanting, the organic phase is washed with a molar solution of hydrochloric acid (20 ml) and with water (3×20 ml) until neutrality is achieved. After drying the organic phase over magnesium sulphate, followed by filtration and concentration under vacuum, the residue is purified on a silica gel column (eluant: dichloromethane/methanol: 9/1). The expected product is obtained in the form of a colourless oil with a yield of 42% (1.57 g).

후처리

  1. customThe orange-coloured solution obtained
  2. customAfter decanting
  3. washthe organic phase is washed with a molar solution of hydrochloric acid (20 ml) and with water (3×20 ml) until neutrality
  4. dry with materialAfter drying the organic phase over magnesium sulphate
  5. filtrationfollowed by filtration and concentration under vacuum
  6. customthe residue is purified on a silica gel column (eluant: dichloromethane/methanol: 9/1)

출처 및 근거

ORD 기록
ord-3d2b27f7903649bf8c4258caa2a66e02
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06809088B2

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