Triethylamine → 4-azido-N-(2-bromoethyl)benzamide

HRID 1717275ノート

反応式

HRID 1717275 の反応式
[N:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].C1C=CC2N(O)N=NC=2C=1.Br.[Br:24][CH2:25][CH2:26][NH2:27].CCN=C=NCCCN(C)C.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[N:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:27][CH2:26][CH2:25][Br:24])=[O:10])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

参加物

9

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27742172-Bromoethylamine hydrobromideHCID 30341844-Azidobenzoic acid

生成物 1

HCID 857754324-azido-N-(2-bromoethyl)benzamide収率 76.6%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Azidobenzoic acid (1.62 g, 9.70 mmol), HOBt (662 mg, 5.15 mmol, 0.5 eq.) and 2-bromoethylamine hydrobromide (2.43 g, 11.6 mmol, 1.2 eq.) were dissolved in DMF (20 ml), WSC (2.28 g, 11.6 mmol, 1.2 eq.) was added, triethylamine (1.62 ml, 11.6 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was diluted with ethyl acetate (70 ml) and hexane (30 ml) and washed with 2% aqueous sodium carbonate solution, saturated aqueous sodium hydrogen carbonate solution, 10% aqueous sodium chloride solution and saturated brine. The aqueous layers were each extracted with ethyl acetate-hexane (2:1, 75 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated at 30° C. or below to give the title compound as a pale-brown solid (2.0 g).

後処理

  1. washwashed with 2% aqueous sodium carbonate solution, saturated aqueous sodium hydrogen carbonate solution, 10% aqueous sodium chloride solution and saturated brine
  2. extractioneach extracted with ethyl acetate-hexane (2:1, 75 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated at 30° C. or below

出典と根拠

ORDレコード
ord-63b58958f5e34dd28affe8f267657c06
出典データセット
uspto-grants-2010_09
特許番号
US07803822B2

反応ノート

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