Sodium hydride → HCID 18461411, compound

HRID 2303840Notes

Reaction equation

HRID 2303840 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[C:9]([CH3:15])[C:8]=1[CH3:16].Cl[C:18]1[CH:19]=[CH:20][C:21]([N+:33]([O-:35])=[O:34])=[C:22]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:23]=1>CN(C)C=O>[CH3:3][O:4][CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([O:14][C:18]2[CH:19]=[CH:20][C:21]([N+:33]([O-:35])=[O:34])=[C:22]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH:23]=2)=[C:9]([CH3:15])[C:8]=1[CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamateHCID 18184922HCID 18184922, compound

Product 1

HCID 18461411HCID 18461411, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.11 g of sodium hydride (55% by weight) were suspended in 300 ml of N,N-dimethylformamide, followed by the addition of 27.5 g of 4-methoxymethoxy-2,3,5-trimethylphenol. The resulting mixture was stirred at room temperature for one hour. To the reaction mixture, 40.1 g of t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate were added in small portions and the mixture was stirred at 120° C. for 2 hours. The reaction mixture was concentrated by evaporation. Water was added to the concentrate, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=5/1), whereby 57.0 g of the title compound were obtained.

Workup

  1. stirringthe mixture was stirred at 120° C. for 2 hours
  2. concentrationThe reaction mixture was concentrated by evaporation
  3. additionWater was added to the concentrate
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e6edc92cc384480e8e5e708c75d38a03
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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