Dimethylformamide → 5-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide

HRID 855675노트

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HRID 855675 반응식
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[C:8]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:9][C:10]([N+:16]([O-:18])=[O:17])=[C:11]([CH:15]=1)[C:12](O)=[O:13].C[N:30](C=O)C>>[CH3:5][O:6][C:7]1[C:8]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:9][C:10]([N+:16]([O-:18])=[O:17])=[C:11]([CH:15]=1)[C:12]([NH2:30])=[O:13]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 216992955-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzoic acid

생성물 1

HCID 216992855-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide

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온도
50 °C

실험 절차

Thionyl chloride (15 ml) and DMF (0.05 ml) were added to 5-methoxy-4-(3-morpholinopropoxy)-2-nitrobenzoic acid (7.54 g). The mixture was heated at 50° C. for 1 hour, the excess thionyl chloride was removed by evaporation and by azeotroping with toluene (x2). The resulting solid was suspended in THF (200 ml) and ammonia was bubbled through the mixture for 30 minutes. The precipitate was removed by filtration and washed with THF. After concentration of the filtrate by evaporation, the product crystallised and was collected by filtration to give 5-methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide (5.25 g) as light yellow crystals which were used without further purification.

후처리

  1. customthe excess thionyl chloride was removed by evaporation
  2. customby azeotroping with toluene (x2)
  3. customammonia was bubbled through the mixture for 30 minutes
  4. customThe precipitate was removed by filtration
  5. washwashed with THF
  6. customAfter concentration of the filtrate by evaporation
  7. customthe product crystallised
  8. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-97483e019eff4917b0c22f8de8202c76
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262201B1

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