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

HRID 1717355노트

반응식

HRID 1717355 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 21029708N-ethyl-3-hydroxy-4-nitrobenzamide수율 381.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21226206Ethyl acetate hexane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a032896fcd2c4e8e9a4fa428bcac7dce
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803822B2

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