Diethyl Ether → N-(3-Nitro-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

HRID 1258747Notes

Reaction equation

HRID 1258747 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[F:9][C:10]([F:27])([F:26])[O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:14][CH:13]=1.CCOCC>C[N+]([O-])=O>[N+:7]([C:13]1[CH:14]=[C:15]([CH:24]=[CH:25][C:12]=1[O:11][C:10]([F:9])([F:26])[F:27])[CH2:16][NH:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:22])[CH3:20])([O-:8])=[O:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11073463Nitronium tetrafluoroborateHCID 58129192N-(4-Trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

Product 1

HCID 67975181N-(3-Nitro-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Nitronium tetrafluoroborate (3.97 g, 29.9 mmol) was added in portions over 5 min to N-(4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide (4.1 g, 15 mmol) in MeNO2 (35 mL) and the mixture was stirred at rt for 1 h. The mixture was treated with ice and Et2O was added. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was treated with PE and the sub-title compound was filtered off.

Workup

  1. additionwas added
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe residue was treated with PE
  6. filtrationthe sub-title compound was filtered off

Sources & evidence

ORD record
ord-d552eaf330e64d0b968b7dc66dcb296a
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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