Sodium hydride → 5-(N,N-Dibenzylglycyl)-2-(2-phenoxyethoxy)benzamide

HRID 1974216Notes

Reaction equation

HRID 1974216 reaction equation
[Na].[CH2:2]([N:9]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:10][C:11]([C:13]1[CH:21]=[C:17]([C:18]([NH2:20])=[O:19])[C:16]([OH:22])=[CH:15][CH:14]=1)=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[O:32]([CH2:39][CH2:40]Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O.C(OCC)(=O)C.O>[CH2:23]([N:9]([CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([O:22][CH2:40][CH2:39][O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:17]([CH:21]=1)[C:18]([NH2:20])=[O:19])=[O:12])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 68526Benzene, (2-bromoethoxy)-HCID 1217275-((Bis(benzyl)amino)acetyl)salicylamideHCID 5360545Sodium

Product 1

HCID 214888805-(N,N-Dibenzylglycyl)-2-(2-phenoxyethoxy)benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the sodium salt from 5-(N,N-dibenzylglycyl)-salicylamide (10 g) and sodium hydride (0.7 g) in dimethylformamide (50 ml) was heated at 100° for 2 hours with 2-phenoxyethyl bromide (6 g. ). The solution was evaporated under reduced pressure gave a yellow residue that was dissolved in ethyl acetate and water. The organic solution was washed three times with water, dried (MgSO4) and evaporated to leave the crude ether as a yellow oily solid, which was recrystallised from ethanol (150 ml) to give colourless plates (4.6 g) m.p. 146°-147°.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customgave a yellow residue that
  3. washThe organic solution was washed three times with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto leave the crude ether as a yellow oily solid, which
  7. customwas recrystallised from ethanol (150 ml)
  8. customto give colourless plates (4.6 g) m.p. 146°-147°

Sources & evidence

ORD record
ord-57a82d2df1ba49ce89b228195e2700de
Source dataset
uspto-grants-1976_12
Patent number
US04000192

Reaction notes

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