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

HRID 1597211ノート

反応式

HRID 1597211 の反応式
S(Cl)(Cl)=O.FC(F)(F)C(O)=O.[CH3:12][O:13][C:14]1[C:15]([O:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:16][C:17]([N+:23]([O-:25])=[O:24])=[C:18]([CH:22]=1)[C:19](O)=[O:20].C[N:37](C=O)C>>[CH3:12][O:13][C:14]1[C:15]([O:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:16][C:17]([N+:23]([O-:25])=[O:24])=[C:18]([CH:22]=1)[C:19]([NH2:37])=[O:20]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 694655255-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzoic acid trifluoroacetate

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 trifluoroacetate (7.54 g, 16.6 mmol). 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, washed with THF and discarded. 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, 93%yield) 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-1a159c0451944bac854ef2102f7a5fe1
出典データセット
uspto-grants-2001_09
特許番号
US06294532B1

反応ノート

読み込み中…