Thionyl Chloride → 5-(Chloromethyl)uracil

HRID 2211817Notes

Reaction equation

HRID 2211817 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1>O1CCOCC1>[Cl:3][CH2:6][C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 781685-(Hydroxymethyl)uracil

Product 1

HCID 2361255-(Chloromethyl)uracilYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Thionyl chloride ((10 ml) was added to a suspension of 5-(hydroxymethyl)-2,4(1H,3H)-pyrimidinedione (0.60 g, 4.2 mmol)from step (11a) in dioxane (15 ml). The reaction was heated to reflux for 4 h, allowed to cool, and concentrated in vacuo to give the 5-(chloromethyl)-2,4(1H,3H)-pyrimidinedione (0.62 g, 100%) as a yellow solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ba52a75ba89449ebaa88639d2057de4
Source dataset
uspto-grants-2006_09
Patent number
US07101883B2

Reaction notes

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