m-Chloroperbenzoic acid → 2-(Chloromethyl)sulfinyl-5-chloropyrimidine

HRID 905235Notes

Reaction equation

HRID 905235 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][CH2:13][S:14][C:15]1[N:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1>C(Cl)(Cl)Cl>[Cl:12][CH2:13][S:14]([C:15]1[N:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 134351352-Chloromethylthio-5-chloropyrimidine

Product 1

HCID 134351372-(Chloromethyl)sulfinyl-5-chloropyrimidineYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-5 °C

Procedure

90% m-chloroperbenzoic acid (4.2 mmol) in chloroform (7 ml) was added dropwise over 40 min to a solution of 2-(chloromethyl)thio-5-chloropyrimidine (3.9 mmol) in chloroform (6 ml) with stirring at -5° C. The mixture was allowed to reach room temperature and stirred overnight, washed with 1 M K2CO3, the dried (MgSO4) chloroform solution evaporated and the residue recrystallized from benzene/petroleum ether (60°-80° C.); yield 73%, m.p. 90° C. 1H NMR (CDCl3): δ4.70 and 5.00 (2H-CO2SO, Jgem 10 Hz), 8.84 (H-4, H-6).

Workup

  1. customto reach room temperature
  2. stirringstirred overnight
  3. washwashed with 1 M K2CO3
  4. dry with materialthe dried (MgSO4) chloroform solution
  5. customevaporated
  6. customthe residue recrystallized from benzene/petroleum ether (60°-80° C.)

Sources & evidence

ORD record
ord-742c2be0852244c3b0a4ef42f2d4cdc3
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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