2-Amino-4,6-dimethoxy-1,3,5-triazine → Methyl 2-((4,6-dimethoxy-1,3,5-triazin-2-yl)carbamoylsulfamoyl)benzoate

HRID 1659817Notes

Reaction equation

HRID 1659817 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=1.[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([N:25]=[C:26]=[O:27])(=[O:24])=[O:23])=[O:15]>C(Cl)Cl>[CH3:9][O:8][C:6]1[N:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:26]([NH:25][S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:14]([O:13][CH3:12])=[O:15])(=[O:24])=[O:23])=[O:27])[N:7]=1

Participants

4

Reactant 2

HCID 278402-Amino-4,6-dimethoxy-1,3,5-triazineHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 187082Methyl 2-((4,6-dimethoxy-1,3,5-triazin-2-yl)carbamoylsulfamoyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.6 g of 2-amino-4,6-dimethoxy-1,3,5-triazine, 25 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate was stirred at ambient temperature for 16 hours. It was then filtered to remove unreacted amine and the filtrate evaporated at temperatures up to 40° under reduced pressure. The residue was triturated with butyl chloride and filtered to yield the desired compound which melted above 170° with decomposition.

Workup

  1. filtrationIt was then filtered
  2. customto remove unreacted amine
  3. customthe filtrate evaporated at temperatures up to 40° under reduced pressure
  4. customThe residue was triturated with butyl chloride
  5. filtrationfiltered

Sources & evidence

ORD record
ord-27a56b4ac7e64c439e9b84bbf905cb54
Source dataset
uspto-grants-1981_12
Patent number
US04305884

Reaction notes

Loading…