Sodium Iodide → 5-(N,N-Dibenzylglycyl)-2-(3-hydroxypropoxy)benzamide

HRID 1974315Notes

Reaction equation

HRID 1974315 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.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:38][CH2:39][CH2:40][OH:41]>CC(=O)CC>[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:13]=[CH:14][C:15]([O:21][CH2:38][CH2:39][CH2:40][OH:41])=[C:16]([CH:20]=1)[C:17]([NH2:19])=[O:18])=[O:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 1217275-((Bis(benzyl)amino)acetyl)salicylamide

Product 1

HCID 214889355-(N,N-Dibenzylglycyl)-2-(3-hydroxypropoxy)benzamideYield 132.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-(N,N-dibenzylglycyl)salicylamide (10.0 g), sodium iodide (4.0 g), potassium carbonate (3.7 g) and 3-chloropropan-1-ol (2.56 g) in butanone (100 ml) was heated under reflux for 24 hours, and filtered to give a cream solid (15.3 g). This was extracted with boiling ethanol and the clear solution was cooled to give a yellow solid (4.0 g) which was crystallised from methanol as colourless crystals (3.4 g). It had m.p. 171°-175°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. filtrationfiltered

Sources & evidence

ORD record
ord-39244b7a906f43bd8e9c14b1ea7295d7
Source dataset
uspto-grants-1976_12
Patent number
US04000193

Reaction notes

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