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

HRID 619911Notes

Reaction equation

HRID 619911 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[CH3:11][O:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22])=[O:14]>C(Cl)Cl>[CH3:9][O:8][C:6]1[N:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:25]([NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:13]([O:12][CH3:11])=[O:14])(=[O:23])=[O:22])=[O:26])[N:7]=1

Participants

4

Reactant 2

HCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 52999Metsulfuron-methyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an anhydrous suspension of 1.4 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 25 ml of methylene chloride was added with stirring at ambient temperature and pressure 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. The mixture was thereafter stirred for 16 hours and filtered. The filtrate was evaporated to dryness, the residue was triturated with butyl chloride and the product removed by filtration. The production thus obtained melted at 165°, and had absorption peaks in the infrared at 1550, 1600, 1680 and 1700 cm-1 and in the NMR spectrum at 2.5, 3.65, 4.0 with an aromatic multiplet at 7.2-8 ppm.

Workup

  1. additionwas added
  2. stirringThe mixture was thereafter stirred for 16 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was triturated with butyl chloride
  6. customthe product removed by filtration
  7. customabsorption peaks in the

Sources & evidence

ORD record
ord-ba167a8e6ffb4abd80d0a1172e1ec573
Source dataset
uspto-grants-1989_04
Patent number
US04818278

Reaction notes

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