3'-acetyl-1-benzyl-2'-hydroxy-1H-tetrazole-5-carboxanilide → HCID 178436404, compound

HRID 325719Notes

Reaction equation

HRID 325719 reaction equation
[C:1]([C:4]1[C:5]([OH:25])=[C:6]([CH:22]=[CH:23][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)[CH3:2]>C(O)(=O)C.[Pd]>[CH2:1]([C:4]1[C:5]([OH:25])=[C:6]([CH:22]=[CH:23][CH:24]=1)[NH:7][C:8]([C:10]1[NH:14][N:13]=[N:12][N:11]=1)=[O:9])[CH3:2]

Participants

4

Reactant 1

HCID 1360663373'-acetyl-1-benzyl-2'-hydroxy-1H-tetrazole-5-carboxanilide

Product 1

HCID 178436404HCID 178436404, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3'-acetyl-1-benzyl-2'-hydroxy-1H-tetrazole-5-carboxanilide (2.6 g) in glacial acetic acid (100 ml) was hydrogenated at 52° C. and 4.1 kg/cm2 for 6 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 recrystallised by dissolving in hot dimethylformamide (7 ml) and slowly adding a large volume of water (100 ml). The colourless solid which crystallised out was collected and discarded as an unwanted by-product. The mother liquor was evaporated under diminished pressure, and the resulting residue was recrystallised from a small volume of aqueous dimethylformamide to give 3'-ethyl-2'-hydroxytetrazole-5-carboxanilide (0.3 g) in the form of pale cream crystals, m.p. 185°-187° C.

Workup

  1. customwas hydrogenated at 52° C.
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customto give a solid residue, which
  5. customwas recrystallised
  6. dissolutionby dissolving in hot dimethylformamide (7 ml)
  7. additionslowly adding a large volume of water (100 ml)
  8. customThe colourless solid which crystallised out
  9. customwas collected
  10. customThe mother liquor was evaporated under diminished pressure
  11. customthe resulting residue was recrystallised from a small volume of aqueous dimethylformamide

Sources & evidence

ORD record
ord-d2bfb87fa9df4218a0876a0af4798499
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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