m-Chloroperbenzoic acid → 5-Chloro-2-(methylsulfinyl)pyrimidine

HRID 905231Notes

Reaction equation

HRID 905231 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([Cl:9])=[CH:5][N:4]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[CH3:1][S:2]([C:3]1[N:8]=[CH:7][C:6]([Cl:9])=[CH:5][N:4]=1)=[O:18]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 47370635-Chloro-2-(methylthio)pyrimidine

Product 1

HCID 204757205-Chloro-2-(methylsulfinyl)pyrimidineYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-methylthio-5-chloropyrimidine (13 mmol) in chloroform (85 ml) was cooled to -20° C. and m-chloroperbenzoic acid (17 mmol) added with stirring. The mixture was stirred for 40 min at -20° C. and for 4 h at 0° C. and left at this temperature overnight. The chloroform solution was then washed with 1 M potassium carbonate (3×10 ml) and the dried (MgSO4) solution evaporated. The residual oily material crystallized on standing; yield 80% m.p. 48° C. (n-heptane). 1H NMR (CDCl3): δ2.93 (Me), 8.83 (2H-4,6).

Workup

  1. stirringThe mixture was stirred for 40 min at -20° C. and for 4 h at 0° C.
  2. washThe chloroform solution was then washed with 1 M potassium carbonate (3×10 ml)
  3. dry with materialthe dried (MgSO4) solution
  4. customevaporated
  5. customThe residual oily material crystallized

Sources & evidence

ORD record
ord-f9014a0cc5d94faaba4bb5f638fa16d3
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

Loading…