2-Amino-4-methoxy-6-methyl-1,3,5-triazine → Metsulfuron-methyl

HRID 464123

Reaction equation

HRID 464123 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](Cl)(=[O:13])=[O:12])([O:3][CH3:4])=[O:2].[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=1.[O-:25][C:26]#[N:27].[Na+]>CN1CCCC1=O.C(=O)(O)[O-].[Na+]>[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH:24][C:26]([NH:27][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:1]([O:3][CH3:4])=[O:2])(=[O:13])=[O:12])=[O:25])[N:18]=1

Participants

6

Reactant 3

HCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 517096Sodium Cyanate

Product 1

HCID 52999Metsulfuron-methylYield 55%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
25 °C

Procedure

A slurry of 10.0 grams (0.042 moles) of 2-carbomethoxybenzenesulfonyl chloride, 5.0 grams (0.0357 moles) 4-methoxy-6-methyl-1,3,5-triazin-2-amine and 6.0 grams (0.092 moles) sodium cyanate in 60 ml N-methylpyrrolidinone was stirred 2 hours at 80° C. The reaction was cooled to 25° C., diluted with 200 ml saturated sodium bicarbonate solution, and filtered. The filtrate was acidified with dilute hydrochloric acid and the product was collected by filtration and dried to give the title compound in 55% yield. The IR spectrum of the title compound was identical to that of an authentic sample prepared as taught in U.S. Pat. No. 4,383,113.

Workup

  1. filtrationfiltered
  2. filtrationthe product was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-b7c299a9824f4439972a45dd4673639e
Source dataset
uspto-grants-1985_10
Patent number
US04546179

Linked notes

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