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Aniline → 2-morpholin-4-ylmethyl-6-nitro-N-phenyl-benzamide

HRID 1625122
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HRID 1625122 반응식
[N:1]1([CH2:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:9]=2[C:10]([OH:12])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[N:1]1([CH2:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:9]=2[C:10]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:12])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1
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참가 물질

6

반응물 4

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 598410692-Morpholin-4-ylmethyl-6-nitro-benzoic acid

생성물 1

HCID 598410842-morpholin-4-ylmethyl-6-nitro-N-phenyl-benzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of compound 6 (0.62 g, 2.3 mmol) in THF (50 mL) was treated with thionyl chloride (0.94 mL), stirred at room temperature for 4 h, and evaporated to dryness. The residue was dissolved in THF (50 mL) and treated with aniline (0.58 mL, 6.4 mmol) and diisopropylethylamine (1.12 mL, 6.4 mmol). The reaction mixture was stirred for 4 h, concentrated, dissolved in dichloromethane (50 mL), washed with saturated aqueous sodium bicarbonate (0.25 mL) and brine (25 mL), dried with sodium sulfate, and concentrated. The crude residue of compound 7 then was purified by flash chromatography (5% methanol in dichloromethane).

후처리

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in THF (50 mL)
  3. stirringThe reaction mixture was stirred for 4 h
  4. concentrationconcentrated
  5. dissolutiondissolved in dichloromethane (50 mL)
  6. washwashed with saturated aqueous sodium bicarbonate (0.25 mL) and brine (25 mL)
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated
  9. customThe crude residue of compound 7 then was purified by flash chromatography (5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-9e68906aacd14451a748d0073254ced9
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08779131B2

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