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

HRID 1039868노트

반응식

HRID 1039868 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 584563064-(3-Iodo-5-nitrophenyl)morpholine수율 80%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b24111b797d64cf6ab9486f31dec842d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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