Pyridine → Pyrazosulfuron-ethyl

HRID 374571Notes

Reaction equation

[O-:1][C:2]#[N:3].[Na+].[NH2:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[N:7]=1.N1C=CC=CC=1.[CH3:22][N:23]1[C:27]([S:28](Cl)(=[O:30])=[O:29])=[C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:25]=[N:24]1>C(#N)C>[CH3:13][O:12][C:10]1[CH:9]=[C:8]([O:14][CH3:15])[N:7]=[C:6]([NH:5][C:2]([NH:3][S:28]([C:27]2[N:23]([CH3:22])[N:24]=[CH:25][C:26]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])(=[O:30])=[O:29])=[O:1])[N:11]=1

Participants

Conditions

Temperature: 45 °C

Procedure

7.27 g of anhydrous sodium cyanate, 15.78 g of 2-amino-4,6-dimethoxypyrimidine, 8.04 g of pyridine and 40 g of dry acetonitrile were mixed together and the mixture was warmed to 45° C. under nitrogen atmosphere. To this mixture was added 28.46 g of 1-methyl-4-ethoxycarbonylpyrazole-5-sulfonylchloride over 2 hours and the reaction mixture was stirred for further 2 hours while maintaining the temperature of 45° C. After the completion of the reaction was identified by liquid chromatography, the reaction product was extracted with 200 g of dichloromethane and 40 g of 5% aqueous sulfuric acid solution. The extracted organic layer was dried over anhydrous magnesium sulfate and then filtered. The organic solvent was removed from the product to obtain 41.30 g (Yield 98%) of the title compound as a solid state.

Workup

temperaturewhile maintaining the temperature of 45° C
extractionthe reaction product was extracted with 200 g of dichloromethane and 40 g of 5% aqueous sulfuric acid solution
dry with materialThe extracted organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
customThe organic solvent was removed from the product

Sources & evidence

ORD record: ord-b46e1e80933241f0a5c255e73e389dc5
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05480993

Reaction notes

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