1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide

HRID 2108754ノート

反応式

HRID 2108754 の反応式
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH2:16].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O>CN(C=O)C.CCOC(C)=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH:16][C:7]([C:4]1[CH:3]=[C:2]([Br:1])[S:6][CH:5]=1)=[O:9]

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 211563-MethoxybenzylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 120399785-Bromothiophene-3-carboxylic acid

生成物 1

HCID 57421982N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-Bromothiophene-3-carboxylic acid (70%) (200 mg, 0.6 mmol of monobromide) was dissolved in DMF with 3-methoxybenzyl amine (0.3 g, 2.2 mmol), EDCI (0.42 g, 2.2 mmol), and HOBt hydrate (0.06 g, 0.4 mmol). The reaction mixture was stirred at room temperature for 3 days, diluted with EtOAc and the organic layer washed with 10% citric acid, saturated sodium bicarbonate, and brine. The organic layer was then dried over sodium sulfate and concentrated to an oil, which was purified by column chromatography on silica (10 to 30 5 EtOAc/hexanes) to give the product as a colorless oil, 195 mg, 0.6 mmol, 100%. 1H NMR 500 MHz (CDCl3) 7.81 (1H, s), 7.35 (1H, s), 7.28 (1H, m), 6.93 (1H, m), 6.87 (2H, m), 6.23 (1H, br s), 4.57 (2H, d), 3.84 (3H, s).

後処理

  1. washthe organic layer washed with 10% citric acid, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. concentrationconcentrated to an oil, which
  4. customwas purified by column chromatography on silica (10 to 30 5 EtOAc/hexanes)

出典と根拠

ORDレコード
ord-a2454307d0784adb8946134a70311ebe
出典データセット
uspto-grants-2009_04
特許番号
US07514448B2

反応ノート

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