Acetic Acid → HCID 178488268, compound

HRID 256349Notes

Reaction equation

HRID 256349 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=O)=[C:8](OC(C)C)[C:7]=2[CH:18]=1.N[C:20]1[NH:24][N:23]=[N:22][N:21]=1.C([N:27](CC)CC)C.C(O)(=O)C>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH2:27])=[O:13])=[C:8]([C:20]3[NH:24][N:23]=[N:22][N:21]=3)[C:7]=2[CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 13961721HCID 13961721, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178488268HCID 178488268, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.7 g (0.023 mole) of 5-methoxy-3-(1-methylethoxy)-2-benzofurancarboxylic acid and 4.2 g (0.026 mole ) of 1,1-carbonylbis(1H-imidazole) in 140 ml of acetonitrile is stirred at reflux for one hour. The mixture is cooled, treated with 2.3 g (0.027 mole) of anhydrous 5-aminotetrazole plus 7.7 ml (5.6 g; 0.055 mole) of triethylamine, and heated at reflux for an additional five hours. The cooled reaction mixture is added to 1.5 kg of ice/water and acidified with glacial acetic acid to precipitate the tetrazole product. The precipitate is filtered, washed with water, and recrystallized from aqueous acetonitrile to yield 6.0 g (82% yield) of the analytically pure 5-methoxy3-tetrazol-5-yl-2-benzofurancarboxamide, mp 241°-245° C.

Workup

  1. temperatureat reflux for one hour
  2. temperatureThe mixture is cooled
  3. temperatureheated
  4. temperatureat reflux for an additional five hours
  5. customThe cooled reaction mixture
  6. customto precipitate the tetrazole product
  7. filtrationThe precipitate is filtered
  8. washwashed with water
  9. customrecrystallized from aqueous acetonitrile

Sources & evidence

ORD record
ord-6e7a265a49c44a3190d1f219e3b62889
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Reaction notes

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