Diisobutylamine → {4-[Bis(2-methylpropyl)amino]-3-nitrophenyl}(phenyl)methanone

HRID 1283386Notes

Reaction equation

HRID 1283386 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1Cl)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])([O-:3])=[O:2].[CH2:19]([NH:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH:20]([CH3:22])[CH3:21]>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N:23]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8085DiisobutylamineHCID 417434-Chloro-3-nitrobenzophenone

Product 1

HCID 23342780{4-[Bis(2-methylpropyl)amino]-3-nitrophenyl}(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 26 g of 3-nitro-4-chloro-benzophenone, 20 ml. of ethanol and 35 ml. of diisobutylamine is heated to 80° to 85 °C under stirring, and the reaction mixture is kept at this temperature for 6 hours. When the reaction is over the ethanol is distilled off under reduced pressure, and 260 ml. of petroleum ether (b.p.: 40° to 100 °C) are added to the solid residue. The separated diisobutylamine hydrochloride is removed by filtration. The filtrate is evaporated, and the residue is recrystallized from ethanol. 32.7 g. of 3-nitro-4-(N,N-diisobutylamino)-benzophenone are obtained; m.p.: 80°-81 °C.

Workup

  1. distillationis distilled off under reduced pressure, and 260 ml
  2. additionof petroleum ether (b.p.: 40° to 100 °C) are added to the solid residue
  3. customThe separated diisobutylamine hydrochloride is removed by filtration
  4. customThe filtrate is evaporated
  5. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-7cf9619bda1844558e3007adde309044
Source dataset
uspto-grants-1976_08
Patent number
US03975390

Reaction notes

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