N,N-Diethylaniline → Ethanone, 1-(4-chloro-3,5-dinitrophenyl)-

HRID 1580530Notes

Reaction equation

HRID 1580530 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14](=[O:16])[CH3:15])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1O)([O-:3])=[O:2].C1(C)C=CC(S([Cl:26])(=O)=O)=CC=1.CCN(C1C=CC=CC=1)CC.[N+](C1C=CC=CC=1)([O-])=O>Cl>[Cl:26][C:9]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]([C:14](=[O:16])[CH3:15])=[CH:7][C:8]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 7061N,N-DiethylanilineHCID 73974-Toluenesulfonyl chlorideHCID 7416NitrobenzeneHCID 104086Ethanone, 1-(4-hydroxy-3,5-dinitrophenyl)-

Product 1

HCID 104087Ethanone, 1-(4-chloro-3,5-dinitrophenyl)-Yield 87.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 22.6 grams (0.1 mole) of 3',5'-dinitro-4'-hydroxyacetophenone, 19.0 grams of p-toluenesulfonyl chloride (0.1 mole), 16.0 grams (0.107 mole) of diethylaniline, and 18.0 grams of nitrobenzene was heated at about 95° C. for 8 hours. The reaction mixture was poured into 200 milliliters of 10 percent aqueous hydrochloric acid and the nitrobenzene steam distilled from the mixture. The residue was cooled to room temperature, the aqueous layer decanted, and the dark oil which slowly solidified (yield 87.5 percent) recrystallized from ethanol (charcoal) to give a pale yellow crystalline compound, melting point 86°-86.5° C.

Workup

  1. distillationthe nitrobenzene steam distilled from the mixture
  2. temperatureThe residue was cooled to room temperature
  3. customthe aqueous layer decanted
  4. customrecrystallized from ethanol (charcoal)
  5. customto give a pale yellow crystalline compound, melting point 86°-86.5° C.

Sources & evidence

ORD record
ord-6ea69dbc96c24180b07a0ad81f92ef98
Source dataset
uspto-grants-1976_01
Patent number
US03933472

Reaction notes

Loading…