Water → N-[2,3,6-Trimethyl-4-[[2-methyl-3-(4-methylphenyl)-2-propenyl]oxy]phenyl]formamide

HRID 272313Notes

Reaction equation

HRID 272313 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][CH:10]=[O:11])=[C:4]([CH3:12])[C:3]=1[CH3:13].[H-].[Na+].Br[CH2:17][C:18]([CH3:27])=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1.O>CN(C)C=O>[CH3:12][C:4]1[C:3]([CH3:13])=[C:2]([O:1][CH2:17][C:18]([CH3:27])=[CH:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[NH:9][CH:10]=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21961295N-(4-hydroxy-2,3,6-trimethylphenyl)formamideHCID 687065381-(3-Bromo-2-methyl-1-propenyl)-4-methylbenzene

Product 1

HCID 73856749N-[2,3,6-Trimethyl-4-[[2-methyl-3-(4-methylphenyl)-2-propenyl]oxy]phenyl]formamideYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-(4-hydroxy-2,3,6-trimethylphenyl)formamide (9.31 g, 52.0 mmol) in N,N-dimethylformamide (120 ml) was added at 0° C. under nitrogen atmosphere sodium hydride (a 60% dispersion in liquid paraffin, 2.11 g, 52.8 mmol) and the resulting mixture was stirred at the same temperature for 10 minutes. To the reaction solution was added a solution of 1-(3-bromo-2-methyl-1-propenyl)-4-methylbenzene (12.48 g, 55.44 mmol) in N,N-dimethylformamide (20 ml) and the resulting mixture was stirred at room temperature for 30 minutes. Water was added into the reaction solution and the product was extracted twice with ethyl acetate. The combined extracts were washed with water, dried on magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was crystallized from ethyl acetate-isopropyl ether to obtain 7.34 g (44% yield) of the title compound. Melting point: 167-169° C.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. extractionthe product was extracted twice with ethyl acetate
  3. washThe combined extracts were washed with water
  4. customdried on magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-bc3405fed0b2487f82414ca9ae7a2da6
Source dataset
uspto-grants-2008_11
Patent number
US07456162B2

Reaction notes

Loading…