Sulfuric Acid → HCID 58226578, compound

HRID 2364795Notes

Reaction equation

HRID 2364795 reaction equation
C(NCC)C.CC(O)(C)C.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)=[O:14].[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].S(=O)(=O)(O)O>[Cl-].[Zn+2].[Cl-].C1C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH2:12][CH2:32][C:31]([C:28]2[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=2)=[O:33])=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 74544-Bromophenacyl bromideHCID 7487p-NitroacetophenoneHCID 8021Diethylamine

Product 1

HCID 58226578HCID 58226578, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

Added benzene (108 mL) to anhydrous zinc(II) chloride (19.62 g, 144 mmol), followed by the addition of diethylamine (11.16 mL, 108 mmol) and 2-methylpropan-2-ol (10.32 mL, 108 mmol) and stirred at room temperature for 2 h. Added 2-bromo-1-(4-bromophenyl)ethanone (20 g, 72.0 mmol) and 1-(4-nitrophenyl)ethanone (17.83 g, 108 mmol) together and stirred mixture for 18 h. Added 5% aq. sulfuric acid (50 mL) and stirred vigorously, then the product was collected by filtration, rinsed with benzene, water, methanol, dichloromethane and dried under vacuum to provide the product (15.0 g, 58% yield, colorless powder).

Workup

  1. stirringstirred vigorously
  2. filtrationthe product was collected by filtration
  3. washrinsed with benzene, water, methanol, dichloromethane
  4. customdried under vacuum
  5. customto provide the product (15.0 g, 58% yield, colorless powder)

Sources & evidence

ORD record
ord-e5709805e8e44bcbb7cb70b54b517d85
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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