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

HRID 855675Notes

Reaction equation

HRID 855675 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-97483e019eff4917b0c22f8de8202c76
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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