Triethylamine → N-ethyl-3-hydroxy-4-nitrobenzamide

HRID 1717355ノート

反応式

HRID 1717355 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.C1C=C[C:17]2N(O)N=[N:20][C:18]=2C=1.Cl.C(N)C.C(N(CC)CC)C.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH2:18]([NH:20][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([OH:1])[CH:3]=1)[CH3:17]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 692653-Hydroxy-4-nitrobenzoic acidHCID 757711-Hydroxybenzotriazole

生成物 1

HCID 21029708N-ethyl-3-hydroxy-4-nitrobenzamide収率 381.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

3-Hydroxy-4-nitrobenzoic acid (6.06 g, 32.1 mmol), HOBt (0.876 g, 6.42 mmol, 0.2 eq.) and ethylamine hydrochloride (3.03 g, 35.3 mmol, 1.1 eq.) were suspended in DMF (80 ml), triethylamine (5.82 ml, 41.7 mmol, 1.3 eq.) was added, WSC (6.91 g, 35.3 mmol, 1.1 eq.) was added, and the mixture was stirred at room temperature for 14.5 hr. The reaction mixture was suspended in ethyl acetate-hexane (4:1, 250 ml) and washed sequentially with 8% acidic solution of ammonium chloride in water (×2), 10% aqueous ammonium chloride solution and saturated brine. The aqueous layers were each extracted with ethyl acetate-hexane (4:1, 150 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated, and the residue was diluted with diethyl ether. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a yellow powder (5.14 g, 24.5 mmol, 76.2%).

後処理

  1. washwashed sequentially with 8% acidic solution of ammonium chloride in water (×2), 10% aqueous ammonium chloride solution and saturated brine
  2. extractioneach extracted with ethyl acetate-hexane (4:1, 150 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionthe residue was diluted with diethyl ether
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with diethyl ether
  8. customdried

出典と根拠

ORDレコード
ord-a032896fcd2c4e8e9a4fa428bcac7dce
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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