Guanidine Nitrate → HCID 178512737, compound

HRID 236649

Reaction equation

HRID 236649 reaction equation
[N+]([O-])(O)=O.[NH2:5][C:6]([NH2:8])=[NH:7].[H-].[Na+].[H][H].Cl[C:14]1[S:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[N:17][N:18]=1>CN(C)C=O.O>[NH:7]([C:14]1[S:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[N:17][N:18]=1)[C:6]([NH2:8])=[NH:5]

Participants

7

Reactant 4

HCID 10481Guanidine NitrateHCID 24758Sodium hydrideHCID 105142772-Chloro-5-(4-nitrophenyl)-1,3,4-thiadiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 178512737HCID 178512737, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

24.13 gm of guanidine nitrate were added in small portions over a period of 30 minutes to 6.5 gm of a 50% sodium hydride oil dispersion in 200 ml of dimethylformamide. After the evolution of hydrogen has ceased, a solution 15.8 gm of 2-chloro-5-(4-nitro-phenyl)-1,3,4-thiadiazole in 300 ml of dimethylformamide was added dropwise to the mixture, which was then stirred at room temperature for 2 hours, and then at 90° C. for 30 minutes. After cooling and dilution with water, the precipitate formed thereby was filtered off and dissolved in ethanol. Hydrogen chloride was added to this solution, and the hydrochloride which separated out was filtered off and dissolved in water, and the aqueous solution was made alkaline with 10% sodium hydroxide. The free base was filtered off, washed with water and dried, yielding 9.5 gm of the title compound, m.p. 295°-297° C.

Workup

  1. waitat 90° C. for 30 minutes
  2. temperatureAfter cooling
  3. filtrationthereby was filtered off
  4. dissolutiondissolved in ethanol
  5. additionHydrogen chloride was added to this solution
  6. customthe hydrochloride which separated out
  7. filtrationwas filtered off
  8. dissolutiondissolved in water
  9. filtrationThe free base was filtered off
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-b1130618595f4ea0bf6f0c74b22af9cf
Source dataset
uspto-grants-1987_02
Patent number
US04645841

Linked notes

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