Benzene → Ethanone, 1-(4-(dipropylamino)-3,5-dinitrophenyl)-

HRID 1580531Notes

Reaction equation

HRID 1580531 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11](=[O:13])[CH3:12])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[CH:17]1[CH:22]=[CH:21]C=CC=1>C(NCCC)CC>[N+:14]([C:3]1[CH:4]=[C:5]([C:11](=[O:13])[CH3:12])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[N:8]([CH2:17][CH2:22][CH3:21])[CH2:7][CH2:6][CH3:5])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 241BenzeneHCID 104087Ethanone, 1-(4-chloro-3,5-dinitrophenyl)-

Product 1

HCID 40241Ethanone, 1-(4-(dipropylamino)-3,5-dinitrophenyl)-

Reagents, catalysts & solvents 1

HCID 8902DipropylamineSolvent

Procedure

To a solution of 8.9 grams (0.0365 mole) of 4'-chloro-3',5'-dinitroacetophenone in 100 milliliters of benzene, 51 milliliters of di-n-propylamine was slowly added with stirring. The resulting mixture was refluxed for 3 hours. The precipitated dipropylamine hydrochloride was separated by filtration. Evaporation of the filtrate to dryness in vacuo yielded a brown solid weighing 11.5 grams (94.5 percent of the theory). Recrystallization from hexane yielded 8.5 grams of an orange colored crystalline compound, melting point 71°-72° C. Anal. calcd. for C14H19N3O5 : C, 54.36; H, 6.19; N, 13.58. Found: C, 54.47; H, 6.25; N, 13.37.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. customThe precipitated dipropylamine hydrochloride was separated by filtration
  3. customEvaporation of the filtrate to dryness in vacuo
  4. customyielded a brown solid
  5. customRecrystallization from hexane

Sources & evidence

ORD record
ord-4beb46c01aab41fdb97836ee1411d7cd
Source dataset
uspto-grants-1976_01
Patent number
US03933472

Reaction notes

Loading…