Morpholine → (3,4-Dinitrophenyl)(morpholino)methanone

HRID 1047550노트

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HRID 1047550 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.C(N(CC)CC)C.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>CN(C=O)C.C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:9])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 107093,4-Dinitrobenzoic acidHCID 24386Thionyl Chloride

생성물 1

HCID 13043973(3,4-Dinitrophenyl)(morpholino)methanone수율 56.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of 3,4-dinitrobenzoic acid (200 mg, 0.943 mmol) and DMF (2 drops) in THF (7 mL) was treated with thionyl chloride (0.14 mL, 224 mmol) and then heated at reflux for 2.5 h. The mixture was cooled to 0° C. and triethylamine (286 mg, 1.883 mmol) was added over 25 min while keeping the internal temperature at 0° C. Morpholine (164 mg, 1.883 mmol) was added. The mixture was stirred overnight and allowed to warm to ambient temperature. Purification by flash chromatography afforded the title compound (150 mg). 1H NMR (400 MHz, CD3OD): δ 8.36 (s, 1H), 8.10 (d, 1H, J=8.8 Hz), 7.28 (d, 1H, J=9.2 Hz), 3.79 (m, 4H), 3.16 (m, 4H).

후처리

  1. temperatureheated
  2. temperatureat reflux for 2.5 h
  3. customat 0° C
  4. temperatureto warm to ambient temperature
  5. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-7d6739403c8740dca5da36cf7d61bf52
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569511B2

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