Water → HCID 178522723, compound

HRID 414462Notes

Reaction equation

HRID 414462 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[NH:15][N:14]=[N:13][N:12]=2)=[O:9])[CH:5]=[N:4][CH:3]=1.O.[OH-].[Na+].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O>[C:20]1([NH:19][C:2]2[N:7]=[C:6]([C:8]([NH:10][C:11]3[NH:15][N:14]=[N:13][N:12]=3)=[O:9])[CH:5]=[N:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 14798Sodium HydroxideHCID 178522716HCID 178522716, compound

Product 1

HCID 178522723HCID 178522723, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 1.13 g of 6-chloro-N-(1H-5-tetrazolyl)pyrazine-2-carboxamide in 5 ml of dimethylsulfoxide, 4.55 ml of aniline was added, and the mixture was heated for 17 hours at 80°-90 ° C. Water and 10%-sodium hydroxide aqueous solution were added to the reaction mixture, and the aqueous alkaline solution was washed with chloroform. The aqueous layer was filtered, and the filtrate was adjusted with 10%-hydrochloric acid to pH 3. The precipitate was collected by filtration, and recrystalized from a mixture of dimethylsulfoxide and ethanol affording 0.80 g of the desired compound as yellow needles, m.p. 290°-293.5° C. (decomp.).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated for 17 hours at 80°-90 ° C
  3. washthe aqueous alkaline solution was washed with chloroform
  4. filtrationThe aqueous layer was filtered
  5. filtrationThe precipitate was collected by filtration
  6. customrecrystalized from a mixture of dimethylsulfoxide and ethanol affording 0.80 g of the desired compound as yellow needles, m.p. 290°-293.5° C. (decomp.)

Sources & evidence

ORD record
ord-75327a79c0a64edb8f15871828de2c97
Source dataset
uspto-grants-1988_12
Patent number
US04792547

Reaction notes

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