Butyl bromide → N-(3-butoxyphenyl)-2-methylbenzamide

HRID 1287694Notes

Reaction equation

HRID 1287694 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].[OH-].[K+].[CH2:20](Br)[CH2:21][CH2:22][CH3:23]>CS(C)=O.O>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 11401898Benzamide, N-(3-hydroxyphenyl)-2-methyl-

Product 1

HCID 180534N-(3-butoxyphenyl)-2-methylbenzamideYield 92.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent3×

Procedure

A 22.7 g (0.1 mol) portion of 3'-hydroxy-2-methylbenzanilide was dissolved in 80 ml of dimethyl sulfoxide and to this solution was added a solution of 5.6 g (0.1 mol) of potassium hydroxide in 40 ml of water. The white mixture was cooled with water, and 30 ml of dimethyl sulfoxide containing 13.7 g (0.1 mol) of n-butylbromide was added dropwise to the solution with stirring. After the addition, the mixture was warmed and kept at 40° to 50° C for 3 hours. The reaction mixture was poured into 700 ml of water and the oily material formed was extracted with benzene. The benzene layer was washed with water, dehydrated over anhydrous sodium sulfate and the benzene was removed to obtain the product, which was recrystallized from a mixture of benzene and n-hexane (1 : 2) to obtain 26.3 g (92.9%) of greyish needle-like crystals having a melting point of 87° C.

Workup

  1. additionwas added dropwise to the solution
  2. additionAfter the addition
  3. temperaturethe mixture was warmed
  4. customthe oily material formed
  5. extractionwas extracted with benzene
  6. washThe benzene layer was washed with water
  7. customthe benzene was removed
  8. customto obtain the product, which
  9. customwas recrystallized from a mixture of benzene and n-hexane (1 : 2)

Sources & evidence

ORD record
ord-f34fb4626f074009a31a87ef4013c609
Source dataset
uspto-grants-1976_10
Patent number
US03985804

Reaction notes

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