1,1'-Carbonyldiimidazole → 3-Methoxy-4,5-dimethy-N-1H-tetrazol-5-yl-2-thiophenecarboxamide

HRID 621796Notes

Reaction equation

HRID 621796 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[C:19]([CH3:20])=[C:18]([CH3:21])[S:17][C:16]=1[C:22]([OH:24])=O.[NH2:25][C:26]1[NH:30][N:29]=[N:28][N:27]=1>O1CCCC1>[CH3:13][O:14][C:15]1[C:19]([CH3:20])=[C:18]([CH3:21])[S:17][C:16]=1[C:22]([NH:25][C:26]1[NH:30][N:29]=[N:28][N:27]=1)=[O:24]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 13061858HCID 13061858, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 1784935763-Methoxy-4,5-dimethy-N-1H-tetrazol-5-yl-2-thiophenecarboxamideYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Carbonyldiimidazole (4.1 g, 25 mmoles) is added to a solution of 3-methoxy-4,5-dimethyl-2-thiophenecarboxylic acid (4.5 g, 24 mmoles) in tetrahydrofuran (80 mL) under argon. The mixture is stirred and heated under reflux for 1.5 hours. 5-Aminotetrazole (2.0 g, 24 mmoles) is added and heating under reflux is continued for an additional 2.5 hours. The mixture is cooled, and the precipitate is filtered off, rinsed with tetrahydrofuran, dried, and stirred in 2N HCl. After 10 minutes the suspended solid is collected by filtration, rinsed with water and dried to afford the product (4.4 g); mp 229° C. (dec).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. temperatureThe mixture is cooled
  6. filtrationthe precipitate is filtered off
  7. washrinsed with tetrahydrofuran
  8. customdried
  9. stirringstirred in 2N HCl
  10. filtrationAfter 10 minutes the suspended solid is collected by filtration
  11. washrinsed with water
  12. customdried

Sources & evidence

ORD record
ord-5941bea248584bf2a40073fb2af84824
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

Loading…