Thionyl Chloride → 4,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

HRID 1454464Notes

Reaction equation

HRID 1454464 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[N:9]O)=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.O=S(Cl)Cl>>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 218222514,6-Dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde oxime

Product 1

HCID 42016204,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileYield 93%

Conditions

Temperature
75 °C

Procedure

To 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde oxime (2.38 g, 10 mmol) was added SOCl2 (21.8 mL, 0.30 mol) slowly at room temperature. The solution was then heated at 75° C. for about 3 hours before it was concentrated under vacuum. The residue SOCl2 was removed by evaporation with toluene (5 mL) under vacuum. The resulting solid was washed with EtOH/H2O (10 mL, 1:1) to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbonitrile (2.04 g, 93%). LC-MS m/z 220 (M+H)+1.99 minute; 1H-NMR (CDCl3) δ 2.64(3 H).

Workup

  1. concentrationwas concentrated under vacuum
  2. customThe residue SOCl2 was removed by evaporation with toluene (5 mL) under vacuum
  3. washThe resulting solid was washed with EtOH/H2O (10 mL, 1:1)

Sources & evidence

ORD record
ord-e3f0ec6bcb9e40f28b7cf87e8ca60fc4
Source dataset
uspto-grants-2009_01
Patent number
US07479558B2

Reaction notes

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