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

HRID 1666062Notes

Reaction equation

HRID 1666062 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.S(Cl)(Cl)=O>>[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-carbonitrile

Procedure

4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde oxime (7.20 g, 30.38 mmol) was added to neat thionyl chloride (29.63 g, 245 mmol), then the mixture was heated to reflux for 4 hours. The reaction mixture was poured onto ice-water. The precipitate of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile was collected and dried (Yield=6.15 g, 92%). 1H-NMR (300 MHz, CDCl3): δ 2.75 (s, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. additionThe reaction mixture was poured onto ice-water
  4. customThe precipitate of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile was collected
  5. customdried (Yield=6.15 g, 92%)

Sources & evidence

ORD record
ord-c8d00a9692284297bc63e6ee3f370e86
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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