Sulfuryl chloride → 2,4,6-Trichloropyrimidine-5-carbonyl chloride

HRID 1455007Notes

Reaction equation

HRID 1455007 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=[O:10])=[C:4]([Cl:11])[N:3]=1.S(Cl)([Cl:15])(=O)=O>ClC(Cl)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]([C:9]([Cl:15])=[O:10])=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 109327462,4,6-Trichloro-5-pyrimidinecarboxaldehyde

Product 1

HCID 132643612,4,6-Trichloropyrimidine-5-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To the subtitle product of step i) (5.0 g) in dichloroethane (25 ml) was added aza-bis-isobutyronitrile (25 mg) and the mixture heated to 60° C. Sulfuryl chloride (3.67 g) was then added and the reaction heated at 75° C. for 4 h. The same amount of aza-bis-isobutyronitrile (4×25 mg) and sulfuryl chloride (4×3.36 g) was added for 4 days on each day interval. The solvent was evaporated to give a yellow oil which was distilled under reduced pressure to yield the subtitle compound as a yellow oil. Yield 5.8 g.

Workup

  1. temperaturethe reaction heated at 75° C. for 4 h
  2. customThe solvent was evaporated
  3. customto give a yellow oil which
  4. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-052ad9492a7e473c9c7e75c239f8f2fb
Source dataset
uspto-grants-2009_01
Patent number
US07482355B2

Reaction notes

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