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

HRID 1375017ノート

反応式

HRID 1375017 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2fece65c791d457cb6819080d892090d
出典データセット
uspto-grants-2007_01
特許番号
US07166598B2

反応ノート

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