Dimethyl-1,3,5-triazin-2-amine → Methyl 3-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

HRID 1979496Notes

Reaction equation

HRID 1979496 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][O:11][C:12]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[S:19]([N:22]=[C:23]=[O:24])(=[O:21])=[O:20])=[O:13]>C(Cl)Cl>[CH3:9][C:4]1[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:23]([NH:22][S:19]([C:18]2[CH:17]=[CH:16][S:15][C:14]=2[C:12]([O:11][CH3:10])=[O:13])(=[O:20])=[O:21])=[O:24])[N:3]=1

Participants

4

Reactant 2

HCID 15820Dimethyl-1,3,5-triazin-2-amineHCID 1572962-Thiophenecarboxylic acid, 3-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 13390216Methyl 3-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylateYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.23 g of 2-amino-4,6-dimethyl-1,3,5-triazine in 30 ml of anhydrous methylene chloride was added with stirring 2.7 g of 2-methoxycarbonyl-3-thiophenesulfonylisocyanate. The mixture was heated to the boiling point and allowed to cool and stir at ambient temperature for sixteen hours. The solid thus obtained was removed by filtration to yield 2.3 g of the crude desired product melting at 158°-178°. The product showed peaks at 1720 and 1700 cm-1, by infrared absorption spectroscopy, consistent for the desired product.

Workup

  1. temperatureThe mixture was heated to the boiling point
  2. temperatureto cool
  3. customThe solid thus obtained
  4. customwas removed by filtration

Sources & evidence

ORD record
ord-9b8420773c0c424f90a27d5510871c0d
Source dataset
uspto-grants-1984_11
Patent number
US04481029

Reaction notes

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