Water → HCID 178424346, compound

HRID 414463Notes

Reaction equation

HRID 414463 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[C:21]([CH3:26])=[CH:22][CH:23]=[CH:24][CH:25]=1>CS(C)=O>[CH3:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][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

Participants

6

Reactant 4

HCID 962WaterHCID 7242O-ToluidineHCID 14798Sodium HydroxideHCID 178522716HCID 178522716, compound

Product 1

HCID 178424346HCID 178424346, 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, 5.35 ml of o-toluidine was added, and the mixture was heated for 24 hours at 100°-110 ° C. Water and 10%-sodium hydroxide aqueous solution were added to the reaction mixture, and the aqueous alkaline solution was washed with chloroform. 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 dimethylformamide and ethanol affording 0.19 g of the desired compound as dark yellow crystals, m.p. 277°-282° C. (decomp.).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated for 24 hours at 100°-110 ° C
  3. washthe aqueous alkaline solution was washed with chloroform
  4. filtrationAqueous layer was filtered
  5. filtrationThe precipitate was collected by filtration
  6. customrecrystalized from a mixture of dimethylformamide and ethanol affording 0.19 g of the desired compound as dark yellow crystals, m.p. 277°-282° C. (decomp.)

Sources & evidence

ORD record
ord-a0ebc3a374434263b1e70ca2e35b34b5
Source dataset
uspto-grants-1988_12
Patent number
US04792547

Reaction notes

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