3'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide → HCID 178466535, compound

HRID 325724Notes

Reaction equation

HRID 325724 reaction equation
[C:1]([C:4]1[C:5]([OH:26])=[C:6]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[NH:7][C:8]([C:10]1[N:14](CC2C=CC=CC=2)[N:13]=[N:12][N:11]=1)=[O:9])(=[O:3])[CH3:2].[H][H]>C(O)(=O)C.[Pd]>[C:1]([C:4]1[C:5]([OH:26])=[C:6]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[NH:7][C:8]([C:10]1[NH:14][N:13]=[N:12][N:11]=1)=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 1360453873'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilideHCID 178418361HCID 178418361, compound

Product 1

HCID 178466535HCID 178466535, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide (5.0 g) in glacial acetic acid was hydrogenated at 4.1 kg/cm2 and 28° C., using a 5% w/w palladium on charcoal catalyst. The reaction was carefully monitored, and when the theoretical quantity of hydrogen had been used (after 9.5 hours) the catalyst was filtered off and extracted with acetic acid in a Soxhlet apparatus. The acetic acid solutions were then combined and evaporated, and the resulting residue was recrystallised from a mixture of dimethylformamide and water to give 3'-acetyl-2'-hydroxy-5'-methyltetrazole-5-carboxanilide (2.2 g), m.p. 257° C. (with decomposition).

Workup

  1. customwas hydrogenated at 4.1 kg/cm2 and 28° C.
  2. custom(after 9.5 hours)
  3. filtrationwas filtered off
  4. extractionextracted with acetic acid in a Soxhlet apparatus
  5. customevaporated
  6. customthe resulting residue was recrystallised from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-c7757322d884411cb4b0a798d9e8a3d0
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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