Allyl chloride → 2-(Allylthio)pyrimidine

HRID 2103949Notes

Reaction equation

HRID 2103949 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(O[K])C.Cl[CH2:13][CH:14]=[CH2:15]>C(O)C>[CH2:15]([S:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 178418793HCID 178418793, compoundHCID 178473702HCID 178473702, compound

Product 1

HCID 36805722-(Allylthio)pyrimidineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 mmole of 2-mercaptopyrimidine was dissolved in 20 ml of ethanol in stirring. 10 mole of EtOK was added to the solution, stirred for 5 minutes. At last, about 20 mmole (Not more than 30 mmole) of 3-chloropropylene was added, and stirred overnight. The white precipitate was removed by filtration, the solvent in the filtrate was removed in vacuum. The obtained viscous liquid was separated with a Si gel column (solvents: 1 ethylacetate/3 hexane). 1H NMR (CD3Cl): δ(ppm) 8.39 (2H, d, JH-H=4.74), 6.86 (1H, t, JH-H=4.74), 5.89 (1H, m), 5.20 (1H, d, JH-H=17.00), 5.00 (1H, d, JH-H=9.97), 3.71 (2H, d, JH-H=6.83). Yield: 90%.

Workup

  1. stirringstirred for 5 minutes
  2. stirringstirred overnight
  3. customThe white precipitate was removed by filtration
  4. customthe solvent in the filtrate was removed in vacuum
  5. customThe obtained viscous liquid was separated with a Si gel column (solvents: 1 ethylacetate/3 hexane)

Sources & evidence

ORD record
ord-c13eb794720e419da65763a9a0a1251c
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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