Water → HCID 19365504, compound

HRID 849943Notes

Reaction equation

HRID 849943 reaction equation
[NH2:1][C:2]1[C:3]([Cl:21])=[CH:4][C:5]([Cl:20])=[C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=2)[CH:7]=1.O.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[Cl:20][C:5]1[CH:4]=[C:3]([Cl:21])[C:2]([NH:1][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:7][C:6]=1[C:8]1[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 19365503HCID 19365503, compound2×

Product 1

HCID 19365504HCID 19365504, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Then, 0.15 g of 3-(5-amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-334) was dissolved in 0.88 ml of pyridine, to which 52 μl of methanesulfonyl chloride was added dropwise, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was poured into water, followed by extraction with chloroform. The organic layer was washed with 2N hydrochloric acid, water, saturated sodium hydrogen-carbonate solution, and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 45 mg (yield, 25%) of 3-(2,4-dichloro-5-methanesulfonylaminophenyl)1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-343; m.p., 189.2° C.).

Workup

  1. additionwas added dropwise
  2. customAfter completion of the reaction
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with 2N hydrochloric acid, water, saturated sodium hydrogen-carbonate solution
  5. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59980ab4f5f246f8aa7743743369e904
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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