Hexamethylphosphoramide → N-methyl-4-cyano-3-nitrobenzamide

HRID 1844788

Reaction equation

HRID 1844788 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[CH3:15][N:16](C)P(=O)(N(C)C)N(C)C>>[CH3:1][NH:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:15]#[N:16])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

3

Reactant 2

HCID 12679HexamethylphosphoramideHCID 207555454-iodo-N-methyl-3-nitrobenzamide

Product 1

HCID 57331535N-methyl-4-cyano-3-nitrobenzamideYield 55.2%

Conditions

Temperature
100 °C

Procedure

2 g (6.53 mmol) N-methyl-4-iodo-3-nitrobenzamide (Compound VII-1), 0.09 g (10.0 mmol) cuprous cyanide and 10 ml hexamethylphosphoric triamide were added into a reaction flask. The mixture was heated to 100° C. and reacted for 40 minutes, and after completing the reaction, the mixture was cooled to room temperature, and then extracted with ethyl acetate. The organic layer was washed with water for three times, dried over anhydrous sodium sulfate, decolorized with activated charcoal, filtered, and the filtrate was concentrated to dryness, recrystallized from ethyl acetate to obtain 0.74 g N-methyl-4-cyano-3-nitrobenzamide (Compound I-27), yield 55.2%.

Workup

  1. customreacted for 40 minutes
  2. customthe reaction
  3. temperaturethe mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water for three times
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated to dryness
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2883e507c52c425595d2a93084f6f789
Source dataset
uspto-grants-2015_02
Patent number
US08946478B2

Linked notes

Loading…