Sodium Iodide → 2-(Iodomethyl)thio-5-chloropyrimidine

HRID 905212Notes

Reaction equation

HRID 905212 reaction equation
[I-:1].[Na+].Cl[CH2:4][S:5][C:6]1[N:11]=[CH:10][C:9]([Cl:12])=[CH:8][N:7]=1>CC(C)=O>[I:1][CH2:4][S:5][C:6]1[N:11]=[CH:10][C:9]([Cl:12])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 134351352-Chloromethylthio-5-chloropyrimidine

Product 1

HCID 134351362-(Iodomethyl)thio-5-chloropyrimidineYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (30 mmol) was added to a solution of 2-chloromethylthio-5-chloropyrimidine (6.7 mmol) in acetone (30 ml) and the mixture heated under reflux for 4 h. The precipitated sodium chloride was removed by filtration, the filtrate evaporated to dryness, the residue triturated with water and recrystallized from ethanol; yield 86%, m.p. 67° C. 1H NMR (CDCl3): δ4.82 (SCH2), 8.67 (H-4, H-6).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 4 h
  3. customThe precipitated sodium chloride was removed by filtration
  4. customthe filtrate evaporated to dryness
  5. customthe residue triturated with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-12f0f7dc480e4c4da921b92593113ada
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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