Phosphorus pentachloride → HCID 24976598, compound

HRID 1287211Notes

Reaction equation

HRID 1287211 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([O-:16])=O.P(Cl)(Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[C:12]([CH2:13][C:14]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10])=[O:16])([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 69157Benzenamine, N-methyl-2-nitro-HCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 24976598HCID 24976598, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

75 g of N-methyl o-nitro aniline and 70 g. of monoethyl malonate (obtained according to M. Freund, Ber. 17, 780, 1884) are dissolved in 550 cc. of benzene, the solution is agitated and 106 g. of phosphorus pentachloride are added, while maintaining the temperature at 20°-23° C.; this is agitated for three hours at room temperature, then heated for 1 hour at 70° C.; a yellow precipitate forms, which dissolves again, giving an orange solution; a water-ice mixture is added, while agitating, to obtain a volume of 1,500 cc., keeping the temperature at 30° C.; the benzene phase is decanted off, washed with water, then with a saturated aqueous solution of sodium bicarbonate and finally with water, dried over sodium sulfate and evaporated under reduced pressure; the residue is purified by recrystallisation in the xylol-petroleum ether mixture (2.5-1). The compound melts at 54°-55° C.

Workup

  1. temperaturewhile maintaining the temperature at 20°-23° C.
  2. temperatureheated for 1 hour at 70° C.
  3. dissolutiona yellow precipitate forms, which dissolves again
  4. customgiving an orange solution
  5. stirringwhile agitating
  6. customto obtain a volume of 1,500 cc
  7. customat 30° C.
  8. customthe benzene phase is decanted off
  9. washwashed with water
  10. dry with materialwith a saturated aqueous solution of sodium bicarbonate and finally with water, dried over sodium sulfate
  11. customevaporated under reduced pressure
  12. customthe residue is purified by recrystallisation in the xylol-petroleum ether mixture (2.5-1)

Sources & evidence

ORD record
ord-44e577bc3933494aaca4f6b63a3f7fc4
Source dataset
uspto-grants-1976_10
Patent number
US03984398

Reaction notes

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