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

HRID 1625122
ノート
印刷プレビュー

反応式

HRID 1625122 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9e68906aacd14451a748d0073254ced9
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08779131B2

反応ノート

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