Hydrochloric Acid → HCID 178513866, compound

HRID 256348Notes

Reaction equation

HRID 256348 reaction equation
CO[C:3]1[C:7]2[CH:8]=[CH:9][C:10](OC)=[CH:11][C:6]=2[O:5][C:4]=1[C:14]([OH:16])=O.O.N[C:19]1[NH:23][N:22]=[N:21][N:20]=1.Cl.C[N:26](C)C=O>>[NH:20]1[C:19]([C:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[O:5][C:4]=2[C:14]([NH2:26])=[O:16])=[N:23][N:22]=[N:21]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 13682654HCID 13682654, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178513866HCID 178513866, compoundYield 43%

Procedure

A mixture of 5.0 g (0.023 mole) of 3,6-dimethoxy-2-benzofurancarboxylic acid and 8.0 g (0.049 mole) of 1,1-carbonylbis(1H-imidazole) in 60 ml of N,N-dimethylformamide is stirred and warmed on the steam bath for 20 minutes. The mixture is cooled to room temperature, 2.5 g (0.024 mole) of 5-aminotetrazole monohydrate is added, and the new mixture is again heated for 20 minutes. The reaction mixture is cooled, added to 350 g of ice/water and acidified with 4.0 N hydrochloric acid to precipitate the tetrazole product. The precipitate is filtered, washed with 50% aqueous ethanol, and recrystallized from aqueous N,N-dimethylformamide to yield 2.8 g (43% yield) of the analytically pure 3,6-dimethoxy-N- 1Htetrazol-5-yl-2-benzofurancarboxamide, mp 238° C.-dec.

Workup

  1. temperaturewarmed on the steam bath for 20 minutes
  2. temperaturethe new mixture is again heated for 20 minutes
  3. temperatureThe reaction mixture is cooled
  4. customto precipitate the tetrazole product
  5. filtrationThe precipitate is filtered
  6. washwashed with 50% aqueous ethanol
  7. customrecrystallized from aqueous N,N-dimethylformamide

Sources & evidence

ORD record
ord-21f5290a192a423eb8a86eefe54a444b
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Reaction notes

Loading…