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Hydrazine hydrate (1:1) → 4-Chloro-6-hydrazinylpyrimidine

HRID 242235
Notes
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Reaction equation

HRID 242235 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[C:9](Cl)[N:8]=[CH:7][N:6]=1>C(O)C>[Cl:4][C:5]1[CH:10]=[C:9]([NH:2][NH2:3])[N:8]=[CH:7][N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 709434,6-Dichloropyrimidine

Product 1

HCID 2472224-Chloro-6-hydrazinylpyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

11.8 ml (12.1 g, 241.6 mmol) hydrazine hydrate are added dropwise to a solution of 20.0 g (134.3 mmol) 4,6-dichloropyrimidine in ethanol at RT, while stirring. If clouding of the solution occurs during metering in of the hydrazine hydrate, further ethanol (approx. 400 ml) is added. The reaction solution is subsequently stirred at RT for 12 h. For working up, the solid which has precipitated out is filtered off, the residue on the filter is washed twice with 150 ml water each time and twice with 100 ml diethyl ether each time and the product is dried in vacuo. A further crystalline product fraction is obtained from the concentrated mother liquor.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. additionis added
  2. stirringThe reaction solution is subsequently stirred at RT for 12 h
  3. customthe solid which has precipitated out
  4. filtrationis filtered off
  5. washthe residue on the filter is washed twice with 150 ml water each time
  6. dry with materialtwice with 100 ml diethyl ether each time and the product is dried in vacuo
  7. customA further crystalline product fraction is obtained from the concentrated mother liquor

Sources & evidence

ORD record
ord-1facbe122c9b4e5fa1c20e9e1f5f47d3
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653111B2

Reaction notes

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