Water → N-(2,6-difluorophenyl)-1-(4,6-dimethyl-2-pyrimidinyl)-5-methyl-1,2,4-triazole-3-sulphonamide

HRID 477729Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][S:10]([C:13]1[N:17]=[C:16]([CH3:18])[NH:15][N:14]=1)(=[O:12])=[O:11].[H-].[Na+].[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[C:24](Cl)[N:23]=1.O>CN(C)C=O.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][S:10]([C:13]1[N:17]=[C:16]([CH3:18])[N:15]([C:24]2[N:25]=[C:26]([CH3:28])[CH:27]=[C:22]([CH3:21])[N:23]=2)[N:14]=1)(=[O:11])=[O:12]

Participants

Conditions

Temperature: 25 °C

Procedure

N-(2,6-difluorophenyl)-5-methyl-1,2,4-triazole-3-sulphonamide (5 g) (Compound A81) was added in portions to a suspension of sodium hydride (1.37 g in 80% suspension in oil) in dry dimethylformamide (40 ml). The mixture was stirred for 30 minutes at 25° C., 4,6-dimethyl-2-chloropyrimidine (2.6 g) was added, and the mixture was then stirred at 100° C. for 18 hours. The cooled reaction mixture was poured into water, acidified with glacial acetic acid and then extracted with dichloromethane (3×100 ml). The organic phases were dried and evaporated, and the residue was chromatographed (silica/dichloromethane). The product was recrystallised from ethanol to give 0.8 g of the desired product, mp 228°-230° C., identical to that of Example A63.

Workup

stirringthe mixture was then stirred at 100° C. for 18 hours
customThe cooled reaction mixture
extractionextracted with dichloromethane (3×100 ml)
customThe organic phases were dried
customevaporated
customthe residue was chromatographed (silica/dichloromethane)
customThe product was recrystallised from ethanol

Sources & evidence

ORD record: ord-a3dc5b460b5a400a8779ce10e52a86bd
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04889553

Reaction notes

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