Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → 6-[3-(2-Methoxycarbonylphenylsulfonyl)-ureido]-4-methyl-3-methylthio-1,2,4-triazin-5-one

HRID 2291223Notes

Reaction equation

HRID 2291223 reaction equation
[NH2:1][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5]([S:8][CH3:9])=[N:6][N:7]=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]>O1CCOCC1>[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([NH:25][C:26](=[O:27])[NH:1][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5]([S:8][CH3:9])=[N:6][N:7]=1)(=[O:23])=[O:24])=[O:15]

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 115428516-Amino-4-methyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 198565636-[3-(2-Methoxycarbonylphenylsulfonyl)-ureido]-4-methyl-3-methylthio-1,2,4-triazin-5-oneYield 73.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.42 g of 6-amino-4-methyl-3-methylthio-1,2,4-triazin-5-one are suspended in 100 ml of absolute dioxane, and 4.99 g of 2-methoxycarbonylphenylsulfonyl isocyanate are added at room temperature. The reaction proceeds slightly exothermically. After a reaction time of one hour at room temperature, the reaction has ended. The precipitate which has separated out is filtered off and washed with a small amount of dioxane. After drying, 6.0 g of 6-[3-(2-methoxycarbonylphenylsulfonyl)-ureido]-4-methyl-3-methylthio-1,2,4-triazin-5-one with a melting point of 186°-187° C. are thus obtained.

Workup

  1. customAfter a reaction time of one hour
  2. customat room temperature
  3. customThe precipitate which has separated out
  4. filtrationis filtered off
  5. washwashed with a small amount of dioxane
  6. customAfter drying

Sources & evidence

ORD record
ord-5d58e8e3385d436c9b79529576b7c8d9
Source dataset
uspto-grants-1989_01
Patent number
US04795486

Reaction notes

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