1-Hydroxybenzotriazole → 3-methoxy-N-methoxy-N-methyl-4-(trifluoromethyl)benzamide

HRID 1375017노트

반응식

HRID 1375017 반응식
Cl.[CH3:2][NH:3][O:4][CH3:5].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[C:11]([OH:13])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[C:11]([N:3]([O:4][CH3:5])[CH3:2])=[O:13]

참가 물질

8

반응물 6

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 179641303-Methoxy-4-(trifluoromethyl)benzoic acid

생성물 1

HCID 179640593-methoxy-N-methoxy-N-methyl-4-(trifluoromethyl)benzamide수율 91.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N,O-Dimethylhydroxylamine hydrochloride (5.37 g) was added to a mixture of 3-methoxy-4-(trifluoromethyl)benzoic acid (11.0 g), 1-hydroxybenzotriazole (6.76 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.59 g) and N,N-diisopropylethylamine (9.6 ml) in dichloromethane (200 ml), and the whole was stirred at room temperature for 18 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture and the organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with 25% of ethyl acetate in hexane as an eluent to give 3-methoxy-N-methoxy-N-methyl-4-(trifluoromethyl)-benzamide (12.0 g) as a colorless oil.

후처리

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel with 25% of ethyl acetate in hexane as an eluent

출처 및 근거

ORD 기록
ord-2fece65c791d457cb6819080d892090d
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166598B2

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