Hydrogen Peroxide → HCID 12958933, compound

HRID 905240Notes

Reaction equation

HRID 905240 reaction equation
[Se](=O)=O.[OH:4]O.[CH2:6]([S:9][C:10]1[N:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)[C:7]#[CH:8].[Na+].[Cl-]>O.CO>[CH2:6]([S:9]([C:10]1[N:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:4])[C:7]#[CH:8]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 24007Selenium DioxideHCID 12958928HCID 12958928, compound

Product 1

HCID 12958933HCID 12958933, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of selenium dioxide (4 mmol) and 35% H2O2 (4 mmol) in water (2.5 ml) was added to a solution of 2-propargylthio-5-chloropyrimidine in methanol (10 ml). The mixture was stirred at room temperature for 18 h before water (50 ml), saturated with NaCl, was added and the mixture extracted with chloroform (3×20 ml). The dried (MgSO4) chloroform solution was evaporated and the residue recrystallized from chloroform: pet. ether; yield 63%, m.p. 92° C. 1H NMR (CDCl3): δ2.28 (HC≡t, J 2 Hz), 3.87 and 4.09 (CH2J 15 Hz), 8.85 (H-4, H-6), IR (KBr): 3235 (CH≡), 2110 and 2100 (--C≡C--). MS [70 eV; m/e (% rel. int)]: 200 (13, M) 199 (19), 173 (33), 171 (100), 146 (25), 114 (30), 113 (31), 111 (47).

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 recrystallized from chloroform

Sources & evidence

ORD record
ord-91b37290359946ba940f3fa76e83249b
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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