Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → Benzoic acid, 2-(((((6-chloro-3,4-dihydro-4-methyl-3-oxopyrazinyl)amino)carbonyl)amino)sulfonyl)-, methyl ester

HRID 2291222

Reaction equation

HRID 2291222 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12])=[O:4].[NH2:17][C:18]1[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=[C:22]([Cl:24])[N:23]=1>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15](=[O:16])[NH:17][C:18]1[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=[C:22]([Cl:24])[N:23]=1)(=[O:12])=[O:13])=[O:4]

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 130629753-amino-5-chloro-1-methyl-2(1H)-pyrazinone

Product 1

HCID 189318Benzoic acid, 2-(((((6-chloro-3,4-dihydro-4-methyl-3-oxopyrazinyl)amino)carbonyl)amino)sulfonyl)-, methyl esterYield 94.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.41 g of 2-methoxycarbonylphenylsulfonyl isocyanate, 1.6 g of 3-amino-5-chloro-1-methylpyrazin-2-one and 40 ml of absolute dioxane is refluxed for 3 hours. The reaction mixture is evaporated to dryness and the residue is crystallized by treatment with acetone. 3.8 g of 3-[3-(2-methoxycarbonylphenylsulfonyl)-ureido]-5-chloro-1-methylpyrazin-2-one with a melting point of 213°-214° C. are thus obtained.

Workup

  1. temperatureis refluxed for 3 hours
  2. customThe reaction mixture is evaporated to dryness
  3. customthe residue is crystallized by treatment with acetone

Sources & evidence

ORD record
ord-5964d87fbd4a4e46a3d23d419f48cdc8
Source dataset
uspto-grants-1989_01
Patent number
US04795486

Linked notes

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