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

HRID 874865
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HRID 874865 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 (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 (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-602680255ebe4913b899b0f3b28c7f7c
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08980901B2

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