2-(Iodomethyl)oxirane → HCID 20475702, compound

HRID 905223Notes

Reaction equation

HRID 905223 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[S:8])[NH:6][CH:7]=1.[CH3:9][C:10](C)([O-:12])[CH3:11].[K+].C(C1OC1)I>CN(C=O)C>[O:12]1[CH2:11][CH:10]1[CH2:9][S:8][C:5]1[N:6]=[CH:7][C:2]([Cl:1])=[CH:3][N:4]=1

Participants

5

Reactant 3

HCID 1646982-(Iodomethyl)oxiraneHCID 71403455-Chloro-2(1H)-pyrimidinethioneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 20475702HCID 20475702, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-chloropyrimidine-2-thione (6.9 mmol) and potassium tert-butoxide (6.9 mmol) was stirred together in anhydrous DMF (40 ml) for 5 min before epiiodohydrin (6.9 mmol) was added. The mixture was stirred at 80° C. for 7 h while small portions of potassium tert-butoxide were added from time to time to maintain a strong basic solution. The solvent was then removed at reduced pressure, the residue triturated with water (50 ml), the insoluble material extracted with chloroform and the dried (MgSO4) chloroform solution evaporated leaving the oily sulfide, yield 29%. This material was chromatographically homogenous and was identified by its spectroscopic properties. 1H NMR (CDCl3): δ2.6-3.4 (5H, m), 8.50 (H-4, H-6).

Workup

  1. additionwas added
  2. additionwere added from time to time
  3. temperatureto maintain a strong basic solution
  4. customThe solvent was then removed at reduced pressure
  5. customthe residue triturated with water (50 ml)
  6. extractionthe insoluble material extracted with chloroform
  7. dry with materialthe dried (MgSO4) chloroform solution
  8. customevaporated

Sources & evidence

ORD record
ord-0c0fc8113e8944a5a11f1ae0cbbb78c7
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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