N-methyl-2-pyrrolidone → 4'-Methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 418378ノート

反応式

HRID 418378 の反応式
CCN=C=NCCCN(C)C.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[C:21]([C:28]([OH:30])=O)[CH:20]=2)=[CH:15][CH:14]=1.C1C=[CH:33][C:34]2[N:39](O)N=N[C:35]=2C=1.CN1[C:46](=[O:47])CCC1>C(Cl)Cl.CN(C=O)C>[CH3:46][O:47][CH2:33][CH:34]([NH:39][C:28]([C:21]1[CH:20]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([CH3:12])=[CH:18][CH:17]=2)[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=1)=[O:30])[CH3:35]

参加物

7

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 532248984'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid

生成物 1

HCID 595997024'-Methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide収率 83.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

EDCI (16.17 g, 84.38 mmol) was added portion wise to a stirred solution of 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (15.49 g, 60.27 mmol), HOBt (11.44 g, 84.38 mmol) and 2-amino-1-methoxy-1-propane (7 ml, 66.31 mmol) in NMP (9.29 ml, 84.38 mmol), CH2Cl2 (180 ml) and DMF (20 ml) at 0° C. The mixture was allowed to warm to room temperature and was stirred at the same temperature for 14 hours. The reaction mixture was washed with 2N HCl, 2N NaOH, saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated under vaccum to give 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide as a yellow oil (16.5 g, 83.5%). MS (M+H)=329.

後処理

  1. washThe reaction mixture was washed with 2N HCl, 2N NaOH, saturated aqueous NaHCO3, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vaccum

出典と根拠

ORDレコード
ord-b13676a167a3429fa7ff37a496de48aa
出典データセット
uspto-grants-2012_01
特許番号
US08093275B2

反応ノート

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