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

HRID 745449

Reaction equation

HRID 745449 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 1710 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-68c73813228b4336bb27d9eb42c7b680
Source dataset
uspto-grants-1986_07
Patent number
US04599103

Linked notes

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