Pyridine → HCID 178522114, compound

HRID 2372694Notes

Reaction equation

HRID 2372694 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]([SH:14])=[N:12][N:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23].[Cl-].[Na+]>CN(C)C=O>[O:24]([C:22]([NH:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]([SH:14])=[N:12][N:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1)=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 15891Phenyl chloroformateHCID 178479082HCID 178479082, compound

Product 1

HCID 178522114HCID 178522114, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 391 g of 1-(3-aminophenyl)- 5-mercaptotetrazole hydrochloride in 800 ml of N,N-dimethylformamide in a nitrogen gas atmosphere, the mixture was cooled to a temperature below 0° C. After adding thereto 302 ml of pyridine, 294 g of phenyl chloroformate were added dropwise to the s-lution while cooling with stirring so that the liquid temperature was not over 0° C. After further stirring the mixture for one hour at a temperature below 0° C., the reaction mixture was added dropwise to 5 liters of a saturated aqueous sodium chloride solution followed by stirring for 30 minutes. Crystals formed were collected by filtration and washed with 2 liters of water to provide 495 g of the desired compound with a yield of 93%.

Workup

  1. temperaturethe mixture was cooled to a temperature below 0° C
  2. additionAfter adding
  3. temperaturewhile cooling
  4. customwas not over 0° C
  5. stirringAfter further stirring the mixture for one hour at a temperature below 0° C.
  6. stirringby stirring for 30 minutes
  7. customCrystals formed
  8. filtrationwere collected by filtration
  9. washwashed with 2 liters of water

Sources & evidence

ORD record
ord-f08aaccb042d4ba7bfc1b57269ec2494
Source dataset
uspto-grants-1992_03
Patent number
US05100761

Reaction notes

Loading…