Hydrogen Peroxide → 2-(2-Hydroxy-3-chloropropyl)sulfinyl-5-chloropyrimidine

HRID 905242Notes

Reaction equation

HRID 905242 reaction equation
[OH:1]O.[OH:3][CH:4]([CH2:14][Cl:15])[CH2:5][S:6][C:7]1[N:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.[Na+].[Cl-]>O.CO>[OH:3][CH:4]([CH2:14][Cl:15])[CH2:5][S:6]([C:7]1[N:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:1]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 204757112-(2-Hydroxy-3-chloropropyl)thio-5-chloropyrimidine

Product 1

HCID 204757502-(2-Hydroxy-3-chloropropyl)sulfinyl-5-chloropyrimidineYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 35% H2O2 (1.7 mmol) and SeO2 (1.7 mmol) in water (2.5 ml) was added to a solution of 2-(2-hydroxy-3-chloropropyl)thio-5-chloropyrimidine (1.7 mmol) in methanol (10 ml). The mixture was stirred at room temperature for 18 h before saturated NaCl aq. (40 ml) was added and the mixture extracted with chloroform (3×20 ml). The dried (MgSO4) chloroform solution was evaporated and the residue crystallized from ethyl acetate; yield 59%; m.p. 170° C. 1H NMR (DMSO-d6): δ3.0-4.4 (6H, m), 9.10 (H-4, H-6). IR (KBr): 3400 (OH), 1060-1070 cm-1 (SO).

Workup

  1. additionwas added
  2. extractionthe mixture extracted with chloroform (3×20 ml)
  3. dry with materialThe dried (MgSO4) chloroform solution
  4. customwas evaporated
  5. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-4e59b8b037f646f3960a1cd475b74dcb
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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