Water → HCID 178426354, compound

HRID 414464Notes

Reaction equation

HRID 414464 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.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1.O.[OH-].[Na+]>CS(C)=O>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][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:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7813p-ToluidineHCID 14798Sodium HydroxideHCID 178522716HCID 178522716, compound

Product 1

HCID 178426354HCID 178426354, 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 15 ml of dimethylsulfoxide, 5.36 g of p-toluidine was added, and the mixture was heated for 18 hours at 80°-90 ° C., and heated for 6 hours at 100°-110 ° C. Water and 10%-sodium hydroxide aqueous solution was 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 dimethylsulfoxide and methanol affording 0.93 g of the desired compound as yellow needles, m.p. 289.5°-294 ° C. (decomp.).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated for 18 hours at 80°-90 ° C.
  3. temperatureheated for 6 hours at 100°-110 ° C
  4. washthe aqueous alkaline solution was washed with chloroform
  5. filtrationAqueous layer was filtered
  6. filtrationThe precipitate was collected by filtration
  7. customrecrystalized from a mixture of dimethylsulfoxide and methanol affording 0.93 g of the desired compound as yellow needles, m.p. 289.5°-294 ° C. (decomp.)

Sources & evidence

ORD record
ord-7ecd13cd35cb4a18ba1c724bd1f209de
Source dataset
uspto-grants-1988_12
Patent number
US04792547

Reaction notes

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