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

HRID 1819385Notes

Reaction equation

HRID 1819385 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[S-:12][C:13]#[N:14].[K+]>CC(O)=O.O>[Cl:1][C:2]1[N:7]=[C:6]([S:12][C:13]#[N:14])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 2

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

Product 1

HCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateYield 71%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2,4-Dichloro-5-nitropyrimidine (12 g) was dissolved in AcOH (70 mL) and cooled to 0° C. Potassium thiocyanate (6.31 g) was added portion-wise to the solution over 2 h. The reaction was diluted with water and filtered. The filter cake was washed with cold ether to afford the desired 2-chloro-5-nitro-4-thiocyanatopyrimidine (9.5 g, 71%).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with cold ether

Sources & evidence

ORD record
ord-4801511dc9574765841f1bacdc39a0dc
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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