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

HRID 358118Notes

Reaction equation

HRID 358118 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>>[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

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 109327462,4,6-Trichloro-5-pyrimidinecarboxaldehyde

Product 1

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

Procedure

In a first step, 2,4,6-trichloro-pyrimidine-5-carbaldehyde (I) is reacted with sulfuryl chloride to form 2,4,6-trichloropyrimidine-5-carboxylic acid chloride (II). The acyl chloride (II) is reacted, by a Friedel-Crafts-reaction, with an appropriately substituted benzene to form a 2,4,6-trichloro-pyrimidine-5-yl-aryl-ketone (III). Compound III is reacted with an aromatic amine in the presence of a tertiary amine to form a 2,4-dichloro-5-aroyl-6-arylamino-pyrimidine (IV).

Sources & evidence

ORD record
ord-ab18ff4bc7e04237886fdcb6d9e1d6b4
Source dataset
uspto-grants-1984_08
Patent number
US04464457

Reaction notes

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