Methane → HCID 178497856, compound

HRID 325722Notes

Reaction equation

HRID 325722 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:25][CH3:26])=[O:24])[C:17]=2[OH:27])=[O:14])=[N:11][N:10]=[N:9]1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.C>ClCCl.C(=O)(O)[O-].[K+].C(OCC)(=O)C>[OH:27][C:17]1[C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[NH:15][C:13]([C:12]1[NH:11][N:10]=[N:9][N:8]=1)=[O:14]

Participants

8

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 136399283HCID 136399283, compound

Product 1

HCID 178497856HCID 178497856, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516893Potassium BicarbonateSolvent

Procedure

1-Benzyl-2'-hydroxy-3'-methoxycarbonyl-5'-methyl-1H-tetrazole-5-carboxanilide (3.0 g) was added, with stirring, to a suspension of anhydrous aluminium chloride (3.6 g) in dichloromethane (150 ml). After stirring and heating at reflux for 150 minutes, the mixture was poured into a mixture of ice (100 g), aqueous hydrochloric acid (2 N; 100 ml) and ethyl acetate (100 ml), and stirring was continued for a further period of 2 hours. The remaining insoluble material was filtered off and the organic layer was washed with water (3×20 ml) and dried over anhydrous sodium sulphate. Evaporation of the solvent gave a yellow solid, which was then digested in aqueous potassium bicarbonate solution (5% w/v; 100 ml), and the resulting solution was treated with charcoal and filtered. Acidification of the filtrate gave a solid, which was recrystallised from nitromethane to give 2'-hydroxy-3'-methoxycarbonyl-5'-methyltetrazole-5-carboxanilide (1.2 g), m.p. 238°-240° C.

Workup

  1. temperatureheating
  2. temperatureat reflux for 150 minutes
  3. stirringstirring
  4. filtrationThe remaining insoluble material was filtered off
  5. washthe organic layer was washed with water (3×20 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. customEvaporation of the solvent
  8. customgave a yellow solid, which
  9. filtrationfiltered
  10. customAcidification of the filtrate gave a solid, which
  11. customwas recrystallised from nitromethane

Sources & evidence

ORD record
ord-b2d370caee75452c950ad859cfd2ce53
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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