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

HRID 325718Notes

Reaction equation

HRID 325718 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]>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

4

Reactant 1

HCID 1360453873'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide

Product 1

HCID 178466535HCID 178466535, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3'-acetyl-1-benzyl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide (1.6 g) in glacial acetic acid (73 ml) was hydrogenated at 55° C. and 4.1 kg/cm2 for 12 hours, using a catalyst of palladium on charcoal (5% w/w). The mixture was filtered and the filtrate was evaporated in vacuo to give a solid residue, which was purified by chromatography on a column of silica gel, using a mixture of chloroform, methanol and formic acid (86:10:4 by volume) is eluant. The fastest moving fraction (pale yellow) was collected and further purified by thin layer chromatography on silica gel, using a mixture of chloroform, methanol and formic acid (86:10:4 by volume) as eluant, and the product was recrystallised from aqueous dimethylformamide to give 3'-acetyl-2'-hydroxy-5'-methyltetrazole-5-carboxanilide (0.2 g), m.p. 245°-247° C. (with decomposition).

Workup

  1. customwas hydrogenated at 55° C.
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customto give a solid residue, which
  5. customwas purified by chromatography on a column of silica gel
  6. additiona mixture of chloroform, methanol and formic acid (86:10:4 by volume)
  7. customwas collected
  8. customfurther purified by thin layer chromatography on silica gel
  9. additiona mixture of chloroform, methanol and formic acid (86:10:4 by volume) as eluant
  10. customthe product was recrystallised from aqueous dimethylformamide

Sources & evidence

ORD record
ord-e1493aa379af412eac79142462bb2ac4
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

Loading…