Water → Metsulfuron

HRID 2412381Notes

Reaction equation

HRID 2412381 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][C:17]([NH:19][S:20]([C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([O:27]C)=[O:26])(=[O:22])=[O:21])=[O:18])[N:10]=1.O>CS(C)=O>[CH3:7][O:8][C:9]1[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][C:17]([NH:19][S:20]([C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([OH:27])=[O:26])(=[O:22])=[O:21])=[O:18])[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 52999Metsulfuron-methylHCID 23665647Potassium tert-butoxide

Product 1

HCID 91730MetsulfuronYield 51.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.5 g of potassium tert-butoxide and 1.0 g of methyl 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonylbenzoate in 25 ml of dimethyl sulfoxide was stirred at ambient temperature for 3 hours. The yellow solution was then poured into 250 ml of cold water. The free carboxylic acid was precipitated by the addition of enough concentrated hydrochloric acid to reach pH 3. The crude product was filtered, washed with water and dried in vacuo. Recrystallization from acetonitrile yielded 0.5 g of the title compound, m.p. 157°-158° C. The mass spectrum of this compound exhibited the expected molecular ion at m/e=367. The infrared bands at 3300 cm-1 and 1725 cm-1 are consistent with the desired structure. The nuclear magnetic resonance spectrum showed peaks at 2.5 ppm (triazine CH3), 3.9 ppm (triazine OCH3) and 7.4-8.2 ppm (phenyl). The methyl ester peak present in the starting material was not observed in the spectrum of the product.

Workup

  1. customThe free carboxylic acid was precipitated by the addition of enough concentrated hydrochloric acid
  2. filtrationThe crude product was filtered
  3. washwashed with water
  4. customdried in vacuo
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-8771205f31a04cb28cef486e425ccc93
Source dataset
uspto-grants-1985_01
Patent number
US04492599

Reaction notes

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