Sodium hydride → 5-(N,N-Dibenzylglycyl)-2-[2-(2-ethoxyethoxy)ethoxy] benzamide

HRID 1974215Notes

Reaction equation

HRID 1974215 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.[H-].[Na+].C1(C)C=CC(S(O[CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH3:48])(=O)=O)=CC=1>CN(C)C=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:13]=[CH:14][C:15]([O:21][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH3:48])=[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

5

Reactant 3

HCID 24758Sodium hydrideHCID 1217275-((Bis(benzyl)amino)acetyl)salicylamideHCID 41182322-(2-Ethoxyethoxy)ethyl 4-methylbenzene-1-sulfonate

Product 1

HCID 214888835-(N,N-Dibenzylglycyl)-2-[2-(2-ethoxyethoxy)ethoxy] benzamideYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-(N,N-dibenzylglycyl)salicylamide (10 g.) in dimethylformamide (75 ml) was added dropwise to a stirred suspension of sodium hydride (0.875 g) in dimethylformamide (25 ml). 2-(2 -Ethoxyethoxy)ethyl p-toluenesulphonate (12.75 g) was then added and the solution heated at 100° for 2 hours. The solvent was evaporated to give a yellow oily solid which was partitioned between ethyl acetate and water. The ethyl acetate layer was dried (MgSO4), concentrated to 30 ml and chromatographed on alumina (60 g.). The column was eluted with ethyl acetate (100 ml portions). The first fraction was discarded and the subsequent four fractions yielded an oil (12.2 g) which crystallised from ethanol to give the ether as colourless plates (5.8 g) m.p. 91.5°-92.5°. Recrystallisation of a sample raised the m.p. to 92.5°-94°.

Workup

  1. temperaturethe solution heated at 100° for 2 hours
  2. customThe solvent was evaporated
  3. customto give a yellow oily solid which
  4. customwas partitioned between ethyl acetate and water
  5. dry with materialThe ethyl acetate layer was dried (MgSO4)
  6. concentrationconcentrated to 30 ml
  7. customchromatographed on alumina (60 g.)
  8. washThe column was eluted with ethyl acetate (100 ml portions)

Sources & evidence

ORD record
ord-58455cdef3c54df68bcdce7a881218df
Source dataset
uspto-grants-1976_12
Patent number
US04000192

Reaction notes

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