Potassium thiocyanate → 2-Chloro-5-nitropyrimidin-4-yl thiocyanate

HRID 1363237Notes

Reaction equation

HRID 1363237 reaction equation
[S-:1][C:2]#[N:3].[K+].[Cl:5][C:6]1[N:11]=[C:10](Cl)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][N:7]=1>CCO>[Cl:5][C:6]1[N:11]=[C:10]([S:1][C:2]#[N:3])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateYield 78.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

(compound known, e.g. WO 2003/032994) Potassium thiocyanate (0.97 g, 10 mM) was added to a solution of 2,4-dichloro-5-nitropyrimidine (1.94 g 10, mM) in EtOH (40 mL) cooled to 0° C. via an ice bath. The solution was stirred at 0° C. for 30 min, then the bath was removed and the resulting suspension allowed to come to RT over 60 min, when water (100 mL) was added. The precipitate was collected via filtration, washed with ice cold water, dissolved with DCM, dried (MgSO4), filtered and evaporated to yield the titled compound (1.7 g). NMR CDCl3 1H δ 9.4 (s, 1H) ppm.

Workup

  1. customthe bath was removed
  2. waitto come to RT over 60 min
  3. additionwhen water (100 mL) was added
  4. filtrationThe precipitate was collected via filtration
  5. washwashed with ice cold water
  6. dissolutiondissolved with DCM
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-ca87574a63144db09bde3ca2673cd5ef
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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