Sodium Hydroxide → Sulfometuron

HRID 1789148Notes

Reaction equation

HRID 1789148 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([O:24]C)=[O:23])(=[O:15])=[O:14])=[O:11])[N:3]=1.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([OH:24])=[O:23])(=[O:15])=[O:14])=[O:11])[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 52997Sulfometuron-methyl

Product 1

HCID 52998Sulfometuron

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and 11 ml. of 50% aqueous sodium hydroxide was warmed on a steam bath with shaking; 40 ml. of water was added and heating and shaking continued during the next half hour. The resulting solution was then filtered and the filtrate acidified with hydrochloric acid to pH 2 to yield a precipitate which was isolated by filtration to yield the title compound, 0.7 g melting at 160° with decomposition. The nuclear magnetic resonance spectrum showed resonance peaks for the methyl substituents on the pyrimidine ring at 2.66 ppm and the ring hydrogens at 7.2 to 8.4 ppm. The disappearance of the resonance peak at 4.0 ppm confirmed the conversion of the methyl ester to the carboxy group.

Workup

  1. temperatureheating
  2. stirringshaking
  3. customcontinued during the next half hour
  4. filtrationThe resulting solution was then filtered
  5. customto yield a precipitate which
  6. customwas isolated by filtration

Sources & evidence

ORD record
ord-78754e277bf64816b19f44ca82c06a8b
Source dataset
uspto-grants-1987_08
Patent number
US04687507

Reaction notes

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