Hydrochloric Acid → HCID 178450145, compound

HRID 325721Notes

Reaction equation

HRID 325721 reaction equation
C([N:8]1[C:12]([C:13]([NH:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([C:23](=[O:27])[CH2:24][CH2:25][CH3:26])[C:17]=2[OH:28])=[O:14])=[N:11][N:10]=[N:9]1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[C:23]([C:18]1[C:17]([OH:28])=[C:16]([CH:21]=[C:20]([CH3:22])[CH:19]=1)[NH:15][C:13]([C:12]1[NH:11][N:10]=[N:9][N:8]=1)=[O:14])(=[O:27])[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 136065530HCID 136065530, compound

Product 1

HCID 178450145HCID 178450145, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A stirred solution of 1-benzyl-3'-butyryl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide in dichloromethane (75 ml), heated at reflux, was treated with anhydrous aluminium chloride (2.2 g) over a period of 15 minutes. After heating and stirring for a further hour, the mixture was cooled and treated with aqueous hydrochloric acid (2 N; 50 ml). The resulting suspension was heated at reflux with stirring for 15 minutes and then cooled. The precipitated solid was filtered off and combined with a residue which was subsequently obtained by evaporation of the dichloromethane layer of the filtrate. This combined solid was digested in aqueous sodium carbonate solution (2 N) at 90° C., then filtered to remove insoluble material and acidified by treatment with concentrated hydrochloric acid. Recrystallisation from a mixture of dimethylformamide and water gave 3'-butyryl-2'-hydroxy-5'-methyltetrazole-5-carboxanilide (0.78 g), m.p. 231°-233° C. (with decomposition).

Workup

  1. temperatureat reflux
  2. temperatureAfter heating
  3. temperaturethe mixture was cooled
  4. temperatureThe resulting suspension was heated
  5. temperatureat reflux
  6. stirringwith stirring for 15 minutes
  7. temperaturecooled
  8. filtrationThe precipitated solid was filtered off
  9. customwas subsequently obtained by evaporation of the dichloromethane layer of the filtrate
  10. filtrationfiltered
  11. customto remove insoluble material
  12. customRecrystallisation
  13. additionfrom a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-93ba413641544b6b9cc02828722cdfc8
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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