Sodium hydride → t-Butyl N-methyl-N-[2-nitro-5-(4-trifluoromethylphenoxy)phenyl]carbamate

HRID 2303900Notes

Reaction equation

HRID 2303900 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Cl[C:13]1[CH:14]=[CH:15][C:16]([N+:28]([O-:30])=[O:29])=[C:17]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=1.[H-].[Na+]>CN(C)C=O>[CH3:27][N:19]([C:17]1[CH:18]=[C:13]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=2)[CH:14]=[CH:15][C:16]=1[N+:28]([O-:30])=[O:29])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 678744-(Trifluoromethyl)phenolHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18461356t-Butyl N-methyl-N-[2-nitro-5-(4-trifluoromethylphenoxy)phenyl]carbamateYield 20.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to that described in Reference Example 6, a reaction was carried out using 4-trifluoromethylphenol (3.0 g), t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (4.3 g), sodium hydride (55 wt. %, 1.1 g) and anhydrous N,N-dimethylformamide (70 ml) and the reaction mixture was purified to give the title compound (1.26 g)

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-93127b3f3e694269b3285e610bb41ca7
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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