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

HRID 1047550ノート

反応式

HRID 1047550 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7d6739403c8740dca5da36cf7d61bf52
出典データセット
uspto-grants-2013_10
特許番号
US08569511B2

反応ノート

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