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

HRID 905234Notes

Reaction equation

HRID 905234 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[I: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>[I: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 134351362-(Iodomethyl)thio-5-chloropyrimidine

Product 1

HCID 134351382-(Iodomethyl)sulfinyl-5-chloropyrimidineYield 24%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

90% m-chloroperbenzoic acid 8.4 mmol) in chloroform (8 ml) was added dropwise for 10 min with stirring to a solution of 2-(iodomethyl)thio-5-chloropyrimidine in chloroform (7 ml) at -5° C. The reaction mixture was coloured violet during the addition. The mixture was left at room temperature overnight. The chloroform solution was then extracted with 1 M K2CO3, washed with a little water, then dried (MgSO4) solution evaporated and the product subjected to thick-layer chromatography. 2-(Iodomethyl)sulfinyl-5-chloropyrimidine: yield 24%, m.p. 158° C., IR (KBr): 1050 and 1090 cm-1 (SO).

Workup

  1. additionThe reaction mixture was coloured violet during the addition
  2. extractionThe chloroform solution was then extracted with 1 M K2CO3
  3. washwashed with a little water
  4. dry with materialdried (MgSO4) solution
  5. customevaporated

Sources & evidence

ORD record
ord-1728d571ea434b1aa1242be565c69b80
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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