Hydrochloric Acid → 4-Nitro-N-phenylbenzenecarbohydrazonoyl chloride

HRID 328532Notes

Reaction equation

HRID 328532 reaction equation
C1(N(C(=O)C2C=CC([N+]([O-])=O)=CC=2)N)C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.C1(O)C=CC=CC=1.ClP([N:38]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[N:39]=[C:40]([Cl:50])[C:41]1[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=1)(Cl)=O>C(Cl)(Cl)(Cl)Cl>[C:51]1([NH:38][N:39]=[C:40]([Cl:50])[C:41]2[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=2)[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 996Phenol2×HCID 24819Phosphorus pentachlorideHCID 420284Benzoic acid, 4-nitro-, 1-phenylhydrazideHCID 53919909HCID 53919909, compound

Product 1

HCID 299724-Nitro-N-phenylbenzenecarbohydrazonoyl chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
25 °C

Procedure

A quantity (12.86 g., 0.05 mole) of p-nitrobenzoic acid phenylhydrazide, prepared according to the method described by J. Hausknecht, Chem. Ber. 22, p. 324 (1889), was added to a suspension of 10.41 g. (0.05 mole) phosphorus pentachloride in 75 ml. carbon tetrachloride, and the resulting suspension was heated to the reflux temperature. Heating at the reflux temperature was continued until evolution of hydrogen chloride gas ceased. After cooling the reaction mixture to about 25° C., it was poured into an ice-cold suspension of 15.5 g. (0.17 mole) of phenol in 50 ml. carbon tetrachloride. When the reaction between the phenol and the p-nitrobenzoyl chloride (dichlorophosphinyl)phenylhydrazone intermediate was completed, the carbon tetrachloride solvent and other volatile components were removed by evaporation under reduced pressure at 30° C. The resulting suspension of p-nitrobenzoyl chloride phenylhydrazone in triphenyl phosphate was filtered and the filter cake comprising the p-nitrobenzoyl chloride phenylhydrazone was washed with 100 ml. carbon tetrachloride, 50 ml. methanol, and 50 ml. ether. The solid on the filter was recrystallized from a solvent mixture consisting of 100 ml. benzene and 300 ml. naphtha (boiling range 203° to 212° F.). There was thus obtained 4.10 g. of p-nitrobenzoyl chloride phenylhydrazone having a melting point of 156° to 157.5° C. A second recrystallization from a mixture of benzene and Skellysolve C gave the compound melting at 157° to 158.5° C.

Workup

  1. addition324 (1889), was added to a suspension of 10.41 g
  2. temperatureHeating at the reflux temperature
  3. customthe carbon tetrachloride solvent and other volatile components were removed by evaporation under reduced pressure at 30° C
  4. additionThe resulting suspension of p-nitrobenzoyl chloride phenylhydrazone in triphenyl phosphate
  5. filtrationwas filtered
  6. washwas washed with 100 ml
  7. customThe solid on the filter was recrystallized from a solvent mixture
  8. customA second recrystallization
  9. additionfrom a mixture of benzene and Skellysolve C

Sources & evidence

ORD record
ord-680eba2b0416426ba55979d7ebd4332f
Source dataset
uspto-grants-1977_04
Patent number
US04017540

Reaction notes

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