Hydrochloric Acid → HCID 11977260, compound

HRID 2083006Notes

Reaction equation

HRID 2083006 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O-])=O.P(Cl)(Cl)(Cl)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[ClH:24]>C(O)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:6]2[O:7][N:1]=[C:4]3[C:5]=2[CH:8]=[C:9]([Cl:24])[CH:10]=[CH:11]3)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 111012-NitrobenzaldehydeHCID 24813Phosphorus oxychloride

Product 1

HCID 11977260HCID 11977260, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 100 g (0.662 mole) of o-nitrobenzaldehyde and 160 g (1.05 mole) of phosphorus oxychloride was added dropwise with stirring 100 g (1.08 mole) of aniline, keeping the temperature below 30°. After 3 hr. at room temperature it was heated to 75° for 18 hr. and at 90° for 3 hr. (The reaction becomes exothermic when heated). The mixture was cooled, 200ml of ethanol and 200 ml of concentrated hydrochloric acid were added, then heated to reflux for 3 hr. with stirring. On cooling, the precipitate formed was collected and washed with acetone, then resuspended in dilute ammonium hydroxide for 1 hr. and collected again. After crystallization from ethanol, 70 g (86%) of product was obtained. Recrystallization from ethanol gave orange rods, mp 208°-211°.

Workup

  1. additionwas added dropwise
  2. customthe temperature below 30°
  3. waitand at 90° for 3 hr
  4. temperatureheated)
  5. temperatureThe mixture was cooled
  6. temperatureheated
  7. temperatureto reflux for 3 hr
  8. temperatureOn cooling
  9. customthe precipitate formed
  10. customwas collected
  11. washwashed with acetone
  12. waitresuspended in dilute ammonium hydroxide for 1 hr
  13. customand collected again
  14. customAfter crystallization from ethanol

Sources & evidence

ORD record
ord-cb3ee84647534e61a82b8d3300c7a6dc
Source dataset
uspto-grants-1978_04
Patent number
US04083948

Reaction notes

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