Sodium Carbonate → 2,4,6-Trichloropyrimidine-5-carboxylic acid

HRID 1609158Notes

Reaction equation

HRID 1609158 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[C:3]=1[C:10](Cl)=[O:11].C(=O)([O-])[O-:14].[Na+].[Na+]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[C:3]=1[C:10]([OH:11])=[O:14]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 132643612,4,6-Trichloropyrimidine-5-carbonyl chloride

Product 1

HCID 200839572,4,6-Trichloropyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 12.35 parts of trichloropyrimidine-5-carbonyl chloride in 200 parts by volume of acetone is stirred into a suspension of 12.12 parts of γ-(β-sulfatoethylsulfonyl)-propylamine in 250 parts by volume of acetone at 0° C. The reaction is carried out at 5° to 10° C., while maintaining a pH of 6.5 by means of 15% strength aqueous sodium carbonate solution. The trichloro-pyrimidine-5-carboxylic acid compound thus obtained of the formula ##STR25## is isolated by evaporation of the solution under reduced pressure. The compound is a solid substance; it is characterized by the following 13C-NMR spectroscopy values in hexadeutero-dimethyl sulfoxide: δ (in ppm)=21.7; 37.9; 51.2; 52.3; 60.0; 129.4; 157.5; 159.4; 160.6 compared with tetramethylsilane as the internal standard.

Workup

  1. customis carried out at 5° to 10° C.

Sources & evidence

ORD record
ord-0d1725c573794696b56a8739192d6156
Source dataset
uspto-grants-1995_03
Patent number
US05399674

Reaction notes

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