Hydrochloric Acid → HCID 178458117, compound

HRID 621797Notes

Reaction equation

HRID 621797 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Br:13][C:14]1[C:15]([O:22][CH:23]([CH3:25])[CH3:24])=[C:16]([C:19](O)=[O:20])[S:17][CH:18]=1.[NH2:26][C:27]1[NH:31][N:30]=[N:29][N:28]=1.Cl>O1CCCC1>[Br:13][C:14]1[C:15]([O:22][CH:23]([CH3:25])[CH3:24])=[C:16]([C:19]([NH:26][C:27]2[NH:31][N:30]=[N:29][N:28]=2)=[O:20])[S:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 14154209HCID 14154209, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178458117HCID 178458117, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Carbonyldiimidazole (2.2 g, 14 mmoles) is added to a solution of 4-bromo-3-(1-methylethoxy)-2-thiophenecarboxylic acid (3.5 g, 13 mmoles) in tetrahydrofuran (50 mL) under argon. The mixture is stirred and heated under reflux for 1.5 hours. 5-Aminotetrazole (1.1 g, 13 mmoles) is added, and heating under reflux continued for 2.5 additional hours. The mixture is then stirred into ice water (200 mL) and acidified with concentrated HCl. After 1 hour the precipitate is filtered off, rinsed with water and dried to afford the product (4.1 g); mp 193°-194° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. filtrationAfter 1 hour the precipitate is filtered off
  6. washrinsed with water
  7. customdried

Sources & evidence

ORD record
ord-bee0bb0ce5364b3daecd6fb7a0c4a552
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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