Water → HCID 21966456, compound

HRID 1790203Notes

Reaction equation

HRID 1790203 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][CH3:12])=[CH:6][C:5]=1[NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CS(C)=O>[CH2:19]([N:13]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([CH3:10])=[CH:9][C:4]=1[Br:3])[C:14](=[O:18])[CH:15]([CH3:16])[CH3:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 21966445HCID 21966445, compound

Product 1

HCID 21966456HCID 21966456, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of powdered KOH (1.3 g, 23.13 mmol) in DMSO (25 mL) was stirred at 0° C. for 5 minutes. N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (3.30 g, 11.56 mmol) was added cautiously followed immediately by the addition of benzylbromide (2.75 mL, 23.13 mmol) and the reaction stirred at room temperature for 48 hrs. Water was added and the mixture extracted with ethyl acetate. The organic extract was washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to give 4.3 g of N-benzyl-N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (99% yield). 1H NMR (300 MHz; CDCl3): 1.02 (d, J=6.6 Hz, 3 H), 1.15 (d, J=6.6 Hz, 3 H), 2.16 (s, 3 H), 2.29 (m, 1 H), 3.43 (s, 3 H), 3.85 (d, J=14.1 Hz, 1 H), 5.75 (d, J=14.1 Hz, 1 H), 6.02 (s, 1 H), 7.18–7.27 (m, 5 H), 7.38 (s, 1 H).

Workup

  1. stirringthe reaction stirred at room temperature for 48 hrs
  2. extractionthe mixture extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed successively with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed on silica gel (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-702e68e33e77400490e5eec9993d467b
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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