Sulfuric Acid → HCID 86649114, compound

HRID 2364861Notes

Reaction equation

HRID 2364861 reaction equation
C(NCC)C.CC(O)(C)C.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:14].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][C:26]=1[N+:34]([O-:36])=[O:35].OS(O)(=O)=O>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH2:32][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:14])=[CH:27][C:26]=1[N+:34]([O-:36])=[O:35]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 8021DiethylamineHCID 668402-Bromo-4'-nitroacetophenoneHCID 795964'-Chloro-3'-nitroacetophenone

Product 1

HCID 86649114HCID 86649114, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

To a mixture of zinc chloride (39.1 g, 287 mmol) in benzene (215 mL) was added diethylamine (22.24 mL, 215 mmol) and 2-methylpropan-2-ol (20.57 mL, 215 mmol). The resulting mixture was stirred at rt for 2 h, and 2-bromo-1-(4-nitrophenyl)ethanone (35.0 g, 143 mmol) and 1-(4-chloro-3-nitrophenyl)ethanone (42.9 g, 215 mmol) were added in one portion. The resulting mixture was stirred at rt overnight. Added 5% aq. H2SO4 (50 mL) and stirred vigorously to induce precipitation. The resulting solid was collected by filtration and washed successively with benzene, water, methanol, and CH2Cl2. The solid was dried in vacuo to give the title compound.

Workup

  1. stirringThe resulting mixture was stirred at rt overnight
  2. stirringstirred vigorously
  3. customprecipitation
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed successively with benzene, water, methanol, and CH2Cl2
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-3a9b9de28a90487e974830ad00ecec72
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

Loading…