Trifluoroacetic acid → HCID 178436818, compound

HRID 325723Notes

Reaction equation

HRID 325723 reaction equation
[C:1]([C:4]1[C:5]([OH:29])=[C:6]([CH:24]=[C:25]([CH2:27][CH3:28])[CH:26]=1)[NH:7][C:8]([C:10]1[N:14](CC2C=CC(OC)=CC=2)[N:13]=[N:12][N:11]=1)=[O:9])(=[O:3])[CH3:2].FC(F)(F)C(O)=O.COC1C=CC=CC=1>>[C:1]([C:4]1[C:5]([OH:29])=[C:6]([CH:24]=[C:25]([CH2:27][CH3:28])[CH:26]=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 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 136195697HCID 136195697, compound

Product 1

HCID 178436818HCID 178436818, compoundYield 10.5%

Procedure

A mixture of 3'-acetyl-5'-ethyl-2'-hydroxy-1-(4-methoxybenzyl)-1H-tetrazole-5-carboxanilide (0.41 g), trifluoroacetic acid (15 ml) and methoxybenzene (1.0 g) was heated at reflux for 45 minutes. The mixture was then cooled, and the solvents were removed under reduced pressure. The residue was treated with aqueous ammonia (2 N; 10 ml), washed with diethyl ether (10 ml), and the aqueous layer was separated off, cooled in an ice-bath and acidified by treatment with concentrated hydrochloric acid. The resulting solid was filtered off to give 3'-acetyl-5'-ethyl-2'-hydroxytetrazole-5-carboxanilide (30 mg), m.p. 238°-240° C. (with decomposition).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 minutes
  3. temperatureThe mixture was then cooled
  4. customthe solvents were removed under reduced pressure
  5. additionThe residue was treated with aqueous ammonia (2 N; 10 ml)
  6. washwashed with diethyl ether (10 ml)
  7. customthe aqueous layer was separated off
  8. temperaturecooled in an ice-bath
  9. filtrationThe resulting solid was filtered off

Sources & evidence

ORD record
ord-c5c0717ef3a04dd9a186b522a6769f77
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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