Urea → HCID 21449715, compound

HRID 596430Notes

Reaction equation

HRID 596430 reaction equation
[Cl-].[C:2]1([N+:8]2[C:13]([Cl:14])=[C:12]([Cl:15])[C:11]([NH2:16])=[CH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17]C(N)=O.[OH-].[Na+]>>[Cl-:14].[C:2]1([N+:8]2[C:13]([NH2:17])=[C:12]([Cl:15])[C:11]([NH2:16])=[CH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1176UreaHCID 14798Sodium HydroxideHCID 21449723HCID 21449723, compound

Product 1

HCID 21449715HCID 21449715, compoundYield 82.5%

Procedure

15 parts of 1-phenyl-4-amino-5,6-dichloropyridazinium chloride is slowly introduced into a melt of 50 parts of urea (temperature about 130° C). After 15 minutes the melt is cooled and 150 parts of a 10% by weight caustic soda solution is added. A crystalline substance separates out (melting point 180° to 181° C after having been recrystallized from acetonitrile) which is dissolved in 50 parts of concentrated hydrochloric acid. The hydrochloric acid solution is evaporated and the oil which remains is caused to crystallize with a mixture of butyl acetate and alcohol. 11.5 parts (82.5% of theory) of 1-phenyl-4-amino-5-chloro-6-aminopyridazinium chloride is obtained; C10H10N4Cl2. The substance melts at above 300° C. The chlorine number is 27.9% (calculated 27.65%). The perchlorate melts at 160° to 163° C.

Workup

  1. temperatureAfter 15 minutes the melt is cooled
  2. customA crystalline substance separates out (melting point 180° to 181° C after having been recrystallized from acetonitrile) which
  3. dissolutionis dissolved in 50 parts of concentrated hydrochloric acid
  4. customThe hydrochloric acid solution is evaporated
  5. customto crystallize with a mixture of butyl acetate and alcohol

Sources & evidence

ORD record
ord-196afee97d6c4d4ea734daf7c0507042
Source dataset
uspto-grants-1977_03
Patent number
US04011220

Reaction notes

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