Hydrazine hydrate (1:1) → HCID 18953818, compound

HRID 2379886Notes

Reaction equation

HRID 2379886 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2C(=O)C3=CC=CC=C3[C:10]2=[O:19])[N:5]=[C:4]([C:20]2[N:21]=[C:22]([N:25]=[C:26]([NH2:28])[NH2:27])[S:23][CH:24]=2)[CH:3]=1.O.[NH2:30]N>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]([NH2:30])=[O:19])[N:5]=[C:4]([C:20]2[N:21]=[C:22]([N:25]=[C:26]([NH2:28])[NH2:27])[S:23][CH:24]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18953830HCID 18953830, compound

Product 1

HCID 18953818HCID 18953818, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(4-chloro-6-phthalimidomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (1.10 g) and hydrazine mono-hydrate (400 mg) in ethanol (200 ml) was refluxed for 5 hours. After the solvent and excess hydrazine monohydrate were removed by concentration, water (10 ml) was added to the residue and the suspension was adjusted to pH 2 with 6N-hydrochloric acid. The resulting precipitate was filtered off, washed with water (5 ml) and the filtrate and the washing solution were combined. After the solution was readjusted to pH 4 with aqueous sodium bicarbonate, potassium cyanate (320 mg) was added to the solution and the mixture was stirred for 14 hours at ambient temperature. The reaction mixture was readjusted to pH 4 with 6N-hydrochloric acid, additional potassium cyanate (215 mg) was added and the solution was further stirred for 8 hours. The mixture was made basic to pH 10 with aqueous potassium carbonate. The resulting precipitate was collected by filtration, washed with water and recrystallized from a mixture of N,N-dimethylformamide and water to give 4-(4-chloro-6-ureidomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (0.28 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customAfter the solvent and excess hydrazine monohydrate were removed by concentration, water (10 ml)
  3. additionwas added to the residue
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with water (5 ml)
  6. additionwas added to the solution
  7. additionwas added
  8. stirringthe solution was further stirred for 8 hours
  9. filtrationThe resulting precipitate was collected by filtration
  10. washwashed with water
  11. customrecrystallized from a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-9e7c27c8edab4f5e8db25a28de084115
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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