Methyl iodide → 5-(N,N-dibenzylglycyl)-o-anisamide

HRID 866781Notes

Reaction equation

HRID 866781 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:9][C:10]([C:12]1[CH:20]=[C:16]([C:17]([NH2:19])=[O:18])[C:15]([OH:21])=[CH:14][CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:31](=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[CH2:22]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][C:10]([C:12]1[CH:20]=[C:16]([C:17]([NH2:19])=[O:18])[C:15]([O:21][CH3:31])=[CH:14][CH:13]=1)=[O:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1217275-((Bis(benzyl)amino)acetyl)salicylamide

Product 1

HCID 203185845-(N,N-dibenzylglycyl)-o-anisamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-(N,N-Dibenzylglycyl)salicylamide (37.4 g) was heated at reflux for 2 hours with methyl iodide (10 ml) and anhydrous potassium carbonate (20 g) in ethyl methyl ketone (350 ml). The inorganic salts were filtered off and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with water and again evaporated. The residual oil was crystallised from isopropanol to give 5-(N,N-dibenzylglycyl)-o-anisamide as a white solid, (14 g) m.p. 113°-114° .

Workup

  1. filtrationThe inorganic salts were filtered off
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customagain evaporated
  6. customThe residual oil was crystallised from isopropanol

Sources & evidence

ORD record
ord-3dbfaee30a5140ceba3423c1666c732f
Source dataset
uspto-grants-1978_07
Patent number
US04101579

Reaction notes

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