Thionyl Chloride → 4,6-Dichloropyrimidine-5-carbonitrile

HRID 473409

Reaction equation

HRID 473409 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[N:9]O)=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.O=S(Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 760165164,6-Dichloro-5-pyrimidinecarbaldehyde oxime

Product 1

HCID 5993714,6-Dichloropyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4,6-Dichloro-5-pyrimidinecarbaldehyde oxime (8 g) was dissolved in CHCl3 (40 mL) and treated with SOCl2 (6 mL) for 2 h at rt. The solvent was removed and the residue was dissolved in DCM (5 mL). The resulting solid was filtered and washed with DCM (5 mL). The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography using DCM-hexane (3:1) to give 4,6-dichloro-5-pyrimidinecarbonitrile as a white solid.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in DCM (5 mL)
  3. filtrationThe resulting solid was filtered
  4. washwashed with DCM (5 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2b9a09bac4be41d5a9ac0c90a8a45de4
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Linked notes

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