Anisole → HCID 178436818, compound

HRID 325720Notes

Reaction equation

HRID 325720 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].COC1C=CC=CC=1>FC(F)(F)C(O)=O>[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 2

HCID 7519AnisoleHCID 136195697HCID 136195697, compound

Product 1

HCID 178436818HCID 178436818, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3'-acetyl-5'-ethyl-2'-hydroxy-1-(4-methoxybenzyl)-1H-tetrazole 5-carboxanilide (10.0 g) and methoxybenzene (10.0 g) in trifluoroacetic acid (150 ml) was heated at reflux for 45 minutes, and then the solvent was removed in vacuo. The residue was stirred with diethyl ether (100 ml) for 20 minutes, and the precipitated solid was filtered off and recrystallised from a mixture of dimethylformamide and water to give 3'-acetyl-5'-ethyl-2'-hydroxytetrazole-5-carboxanilide (6.5 g), m.p. 239°-242° C. (with decomposition).

Workup

  1. temperatureat reflux for 45 minutes
  2. customthe solvent was removed in vacuo
  3. filtrationthe precipitated solid was filtered off
  4. customrecrystallised from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-5343b08817074ef3875837e211f5dbf4
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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