Morpholine → 4-(3-Iodo-5-nitrophenyl)morpholine

HRID 410378ノート

反応式

HRID 410378 の反応式
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([I:11])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CS(C)=O>[I:11][C:4]1[CH:3]=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1

参加物

4

反応物 2

HCID 8083MorpholineHCID 2590861-Fluoro-3-iodo-5-nitrobenzene

生成物 1

HCID 584563064-(3-Iodo-5-nitrophenyl)morpholine収率 80%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

To a solution of 1-fluoro-3-iodo-5-nitrobenzene (4.0 g, 15 mmol) in DMSO (7.5 mL) was added morpholine (3.26 mL, 37.5 mmol), and the mixture (which instantly became purple) was heated to 130° C. for 30 min in the microwave. Purification was attempted by directly loading the mixture onto a silica gel column (80 g; load neat w/CH2Cl2 rinse; 100:0 to 60:40 hexanes:EtOAc over 35 minutes) but the mixture crashed at the top of the column and not all the mixture could be loaded. Nonetheless, after an initial spike in pressure, purification was possible, and the residual material was purified in a second purification (24 g; load w/CH2Cl2; 100:0 to 60:40 hexanes:EtOAc over 20 minutes). Concentration of the combined fractions from the two purifications provided 4-(3-iodo-5-nitrophenyl)morpholine (4.01 g, 12.0 mmol, 80%) as a bright yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.99 (s, 1H); 7.67 (s, 1H); 7.47 (s, 1H); 3.89 (m, 4H); 3.26 (m, 4H).

後処理

  1. customPurification
  2. washonto a silica gel column (80 g; load neat w/CH2Cl2 rinse; 100:0 to 60:40 hexanes:EtOAc over 35 minutes)
  3. customNonetheless, after an initial spike in pressure, purification
  4. customthe residual material was purified in a second purification (24 g; load w/CH2Cl2; 100:0 to 60:40 hexanes:EtOAc over 20 minutes)

出典と根拠

ORDレコード
ord-5c3d512774cd48889423c50db6f8cecb
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

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