Hydrochloric Acid → HCID 178504675, compound

HRID 1899082Notes

Reaction equation

HRID 1899082 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](O)=[O:14])=[CH:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:38][C:39]1[NH:43][N:42]=[N:41][N:40]=1.Cl>O1CCCC1.O>[NH:40]1[C:39]([NH:38][C:13]([C:11]2[S:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:9]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)[CH:10]=2)=[O:14])=[N:43][N:42]=[N:41]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 11793932HCID 11793932, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178504675HCID 178504675, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-carboxylic acid (1.0 g) and 1,1'-carbonyldiimidazole (0.45 g) in tetrahydrofuran (15 ml) was refluxed for 1.5 hours. 5-Aminotetrazole (0.226 g) was added and the mixture was refluxed for 3 hours. The mixture was diluted with water (50 ml), acidified with hydrochloric acid, and cooled in an ice-water bath. The precipitates were collected and recrystallized from ethanol to give colorless crystals of N-(5-tetrazolyl)-5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-carboxamide (0.93 g).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperaturethe mixture was refluxed for 3 hours
  3. temperaturecooled in an ice-water bath
  4. customThe precipitates were collected
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-727c0e3184cf4751b8dd7c4f3d977f92
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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