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

HRID 1596273ノート

反応式

HRID 1596273 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-87987e057fe14e67948f0be31e4b8a78
出典データセット
uspto-grants-2001_09
特許番号
US06291455B1

反応ノート

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