2-Amino-4,6-dimethoxy-1,3,5-triazine → Methyl 2-[[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylate

HRID 1462842Notes

Reaction equation

HRID 1462842 reaction equation
[C:1]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11])([O:3][CH3:4])=[O:2].[CH3:16][O:17][C:18]1[N:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([NH2:26])[N:19]=1>C(#N)C>[CH3:25][O:24][C:22]1[N:23]=[C:18]([O:17][CH3:16])[N:19]=[C:20]([NH:26][C:14]([NH:13][S:10]([C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[C:1]([O:3][CH3:4])=[O:2])(=[O:11])=[O:12])=[O:15])[N:21]=1

Participants

4

Reactant 2

HCID 278402-Amino-4,6-dimethoxy-1,3,5-triazineHCID 15591262Methyl 2-[(oxomethylidene)sulfamoyl]cyclopent-1-ene-1-carboxylate

Product 1

HCID 15591266Methyl 2-[[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The sulfonyl isocyanate product of Example 3 (5 g) was diluted to a concentration of 1.5M with dry acetonitrile and 2.0 ml of this solution was added to a stirred suspension of 0.27 g 4,6-dimethoxy-1,3,5-triazine-2-amine in 4.0 ml dry acetonitrile under a nitrogen atmosphere. The mixture was heated briefly on the steam bath until a homogeneous solution resulted, then stirred at ambient temperature for 24 hours. Dilution of the mixture with ether precipitated the product which was collected by filtration and dried to 0.54 g of white crystalline solid; m.p. 168°-169°. An infrared spectrum (nujol) exhibited absorptions at 1730 and 1700 cm-1 and an NMR (60 MHz) spectrum in CDCl3 /DMSO-d6 solution exhibited absorptions at 2.1 (CH2), 3.0 (CH2 ×2), 3.75 (CH3O), 4.0 (CH3O×2), 9.9 (NH), 12.3 (NH) ppm indicating the title compound.

Workup

  1. temperatureThe mixture was heated briefly on the steam bath until a homogeneous solution
  2. customresulted
  3. customDilution of the mixture with ether precipitated the product which
  4. filtrationwas collected by filtration
  5. dry with materialdried to 0.54 g of white crystalline solid

Sources & evidence

ORD record
ord-0cf7a8236dd545998c250eb42b1d3d22
Source dataset
uspto-grants-1984_07
Patent number
US04461640

Reaction notes

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