Hydrochloric Acid → HCID 18953904, compound

HRID 2379878Notes

Reaction equation

HRID 2379878 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[N:10]=[C:11]([N:14]=[C:15]([NH2:17])[NH2:16])[S:12][CH:13]=2)[CH:4]=1.C(=O)([O-])O.[Na+].[O-:23][C:24]#[N:25].[K+].[ClH:27].C(=O)([O-])[O-].[K+].[K+]>O>[ClH:27].[ClH:27].[NH2:16][C:15](=[N:14][C:11]1[S:12][CH:13]=[C:9]([C:5]2[CH:4]=[C:3]([CH2:2][NH:1][C:24]([NH2:25])=[O:23])[CH:8]=[CH:7][N:6]=2)[N:10]=1)[NH2:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 11378442Potassium cyanate2×HCID 18953784HCID 18953784, compound

Product 1

HCID 18953904HCID 18953904, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(4-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (1.09 g) was dissolved in water (10 ml) and the solution was adjusted to pH 4 with aqueous sodium hydrogen carbonate. Potassium cyanate (0.25 g) was added to the solution and the mixture was stirred for one hour at ambient temperature. After the pH was readjusted to 4 with 6N-hydrochloric acid, additional potassium cyanate (0.25 g) was added and the mixture was further stirred for 6 hours. The reaction mixture was made basic with aqueous potassium carbonate and the resulting precipitate was collected by filtration. The crude product was chromatographed on silica gel with use of chloroform-methanol (8:2) as eluent and converted to the dihydrochloride in a usual manner. This salt was recrystallized from an aqueous ethanol to give 2-(diaminomethyleneamino)-4-(4-ureidomethylpyridin-2-yl)thiazole dihydrochloride (0.70 g).

Workup

  1. additionwas added
  2. stirringthe mixture was further stirred for 6 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. customThe crude product was chromatographed on silica gel with use of chloroform-methanol (8:2) as eluent
  5. customThis salt was recrystallized from an aqueous ethanol

Sources & evidence

ORD record
ord-53c70a14a9b642f4af74cfca0d9b6d98
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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