Water → HCID 21966461, compound

HRID 2212609Notes

Reaction equation

HRID 2212609 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14].[OH-].[K+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1.O>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N:11]([CH2:25][C:24]1[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[C:12](=[O:16])[CH:13]([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 21966445HCID 21966445, compound

Product 1

HCID 21966461HCID 21966461, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (6.83 g) in DMSO (40 mL) was added powder KOH (2.68 g, 47.7 mmol) and 4-methoxybenzyl chloride (7.5 g, 47.7 mmol) under argon. The mixture was stirred at room temperature for 17 hours. Water (30 mL) was added and the mixture extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:EtOAc/10:1 t0 3:1) to give 8.72 g of N-(2-bromo-5-methoxy-4-methyl-phenyl)-N-(4-methoxy-benzyl)-isobutyramide (90%). 1H NMR (300 MHz, CDCl3, ppm): δ: 1.00 (d, J=7.03 Hz, 3 H), 1.13 (d, J=6.45 Hz, 3 H), 2.17 (s, 3 H), 2.28 (m, 1 H), 3.48 (s, 3 H), 3.78 (s, 3 H), 3.84 (d, J=14.07 Hz, 1 H), 5.62 (d, J=14.07 Hz, 1 H), 6.06 (s, 1 H), 6.78–6.81 (m, 2 H), 7.10–7.13 (m, 2 H), 7.38 (s, 1 H).

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:EtOAc/10:1 t0 3:1)

Sources & evidence

ORD record
ord-48ad8e395407451e9705d87d2ebdfa06
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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