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

HRID 2036554Notes

Reaction equation

HRID 2036554 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 triturated with DCM (5 mL) to give a white solid, which was filtered and washed with DCM (5 mL). The filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel (dry loading, DCM/hexane, 3/1) to give a white solid. The two solids were combined to provide 4,6-dichloro-5-pyrimidinecarbonitrile.

Workup

  1. customThe solvent was removed
  2. customthe residue triturated with DCM (5 mL)
  3. customto give a white solid, which
  4. filtrationwas filtered
  5. washwashed with DCM (5 mL)
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography on silica gel (dry loading, DCM/hexane, 3/1)
  8. customto give a white solid

Sources & evidence

ORD record
ord-4709e0061c7945fbadbf7c032dcfb0ce
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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