Fenamol → HCID 85893808, compound

HRID 839604Notes

Reaction equation

HRID 839604 reaction equation
[C:1]1([N:7]2[C:11]([NH2:12])=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19]Br)[CH3:16]>CN(C)C=O>[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][NH:12][C:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[N:9][N:10]=1)[CH3:16]

Participants

5

Reactant 3

HCID 21640FenamolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 85893808HCID 85893808, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 1-phenyl-5-amino-1H-tetrazole (10 g.) in dried dimethylformamide (50 ml.) was dropwise added to a suspension of 50% sodium hydride (5.1g.) in dried dimethylformamide (5 ml.) over 15 minutes under ice-cooling, and the mixture was stirred for 30 minutes at ambient temperature. To the resultant mixture was added a solution of bromoacetaldehyde diethyl acetal (13.5 g.) in dried dimethylformamide (15 ml.). The mixture was stirred for 1 hour at ambient temperature and for 2 hours and 20 minutes at 60° C. The reaction mixture was cooled to at ambient temperature, ice-water was added thereto and the mixture was extracted 3 times with ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained oil was purified by column chromatography on silica gel (250 g.) using chloroform as developing solvent to give (1-phenyl-1H-tetrazol-5-yl)aminoacetaldehyde diethyl acetal (11 g.), oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1 hour at ambient temperature and for 2 hours and 20 minutes at 60° C
  3. additionwas added
  4. extractionthe mixture was extracted 3 times with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materiala saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe obtained oil was purified by column chromatography on silica gel (250 g.)

Sources & evidence

ORD record
ord-161d44bb004a4bf58c53eb84fd82d83a
Source dataset
uspto-grants-1978_06
Patent number
US04096263

Reaction notes

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