Dibenzylamine → 5-((Bis(benzyl)amino)acetyl)salicylamide

HRID 866780Notes

Reaction equation

HRID 866780 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1)=[O:4].[CH2:15]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(CC)=O>[CH2:23]([N:22]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][C:3]([C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1)=[O:4])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 1985565-(Bromoacetyl)salicylamide

Product 1

HCID 1217275-((Bis(benzyl)amino)acetyl)salicylamideYield 45%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-Bromoacetyl salicylamide (515 g) was added to a stirred solution of dibenzylamine (750 g) in ethyl methyl ketone (3.0 l). The mixture was heated at reflux for one hour and the dibenzylamine hydrobromide was filtered and dried. The filtrate was allowed to cool, when the crude product crystallised. This was filtered off, dried, and recrystallised from ethyl acetate, (5 l), to give 5-(N,N-dibenzylglycyl)salicylamide as an off-white solid (336 g), m.p. 168°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for one hour
  3. filtrationthe dibenzylamine hydrobromide was filtered
  4. customdried
  5. temperatureto cool
  6. customwhen the crude product crystallised
  7. filtrationThis was filtered off
  8. customdried
  9. customrecrystallised from ethyl acetate, (5 l)

Sources & evidence

ORD record
ord-8be136d62c0548a1be788f742b37722c
Source dataset
uspto-grants-1978_07
Patent number
US04101579

Reaction notes

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