HCID 178474351, compound → HCID 178507948, compound

HRID 256350Notes

Reaction equation

HRID 256350 reaction equation
C([NH:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([NH:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1)=[O:15])(=O)C>C(O)C>[NH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([NH:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1)=[O:15]

Participants

3

Reactant 1

HCID 178474351HCID 178474351, compound

Product 1

HCID 178507948HCID 178507948, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.3 g (0.019 mole) of 3-(acetylamino)N-1H-tetrazol-5-yl-2-benzofurancarboxamide in 50 ml of ethanol plus 50 ml of concentrated (12.0 M) hydrochloric acid is stirred at reflux for two hours. The reaction mixture is cooled in ice to precipitate 3-amino-N-1H-tetrazol-5-yl-2-benzofurancarboxamide. The precipitate is filtered, washed with 50% aqueous ethanol, and recrystallized from aqueous 2-methoxyethanol to yield 2.4 g (53% yield) of the analytically pure 3-amino-N-1H-tetrazol-5-yl-2-benzofurancarboxamide, mp 275° C.-dec.

Workup

  1. concentrationof concentrated (12.0 M) hydrochloric acid
  2. temperatureat reflux for two hours
  3. temperatureThe reaction mixture is cooled in ice
  4. customto precipitate 3-amino-N-1H-tetrazol-5-yl-2-benzofurancarboxamide
  5. filtrationThe precipitate is filtered
  6. washwashed with 50% aqueous ethanol
  7. customrecrystallized from aqueous 2-methoxyethanol

Sources & evidence

ORD record
ord-5944be28f638436d97df17d14d2ea3ac
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Reaction notes

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