Potassium Carbonate → N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]t-butylcarbonylmethoxyamine

HRID 370376Notes

Reaction equation

HRID 370376 reaction equation
[CH3:1][N:2]([OH:24])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[Cl:20])[CH:6]=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+].Br[CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>CC(C)=O>[CH3:1][N:2]([O:24][CH2:32][C:33]([C:34]([CH3:37])([CH3:36])[CH3:35])=[O:38])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:12][C:11]=2[Cl:20])[CH:6]=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 20275650HCID 20275650, compound

Product 1

HCID 54464704N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]t-butylcarbonylmethoxyamine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-methyl-N[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]hydroxyamine (700 mg., 1.93 mm) K2CO3 (320 mg.), 1-bromo-3,3-dimethylbutan-2-one (520 mg.) and acetone (10 ml.) is refluxed for about 16 hours. Then, the mixture is filtered and filtrate concentrated. The concentrate is purified by prep. TLC using 20% ethyl acetate/hexane to give N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]t-butylcarbonylmethoxyamine (IVA; R3 is H, n is one, and R4 is t-butyl).

Workup

  1. temperatureis refluxed for about 16 hours
  2. filtrationThen, the mixture is filtered
  3. concentrationfiltrate concentrated
  4. customThe concentrate is purified by prep

Sources & evidence

ORD record
ord-a02b4fd39bd0475aaea4f7de62175336
Source dataset
uspto-grants-1985_07
Patent number
US04526608

Reaction notes

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