Water → N-(2-Chloro-4-sulfamoyl-phenyl)-2-[5-fluoromethyl-4-(4-methyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamide

HRID 1844283Notes

Reaction equation

HRID 1844283 reaction equation
[F:1][CH2:2][C:3]1[N:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH3:19])=[CH:11][CH:10]=2)[C:5]([SH:8])=[N:6][N:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](=[O:40])(=[O:39])[NH2:38])=[CH:33][C:32]=1[Cl:41])=[O:29].O>CN(C=O)C>[Cl:41][C:32]1[CH:33]=[C:34]([S:37](=[O:40])(=[O:39])[NH2:38])[CH:35]=[CH:36][C:31]=1[NH:30][C:28](=[O:29])[CH2:27][S:8][C:5]1[N:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH3:19])=[CH:11][CH:10]=2)[C:3]([CH2:2][F:1])=[N:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 215288302-chloro-N-(2-chloro-4-sulfamoylphenyl)acetamideHCID 178426263HCID 178426263, compound

Product 1

HCID 66632958N-(2-Chloro-4-sulfamoyl-phenyl)-2-[5-fluoromethyl-4-(4-methyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamideYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a solution of 5-fluoromethyl-4-(4-methyl-naphthalen-1-yl)-4H-[1,2,4]triazole-3-thiol (89 mg, 0.33 mmol), K2CO3 (50.0 mg, 0.36 mmol) in DMF (2.0 mL) was added 2-chloro-N-(2-chloro-4-sulfamoyl-phenyl)-acetamide (93 mg, 0.33 mmol). The reaction mixture was stirred at room temperature for 16 h. Upon the completion of the reaction, H2O (2.0 mL) was added to the reaction and stirred til precipitation occurred and filtered to give solid (126.8 mg, 74% yield). 1H NMR (DMSO, 300 MHz) δ 10.12 (broad s, 1H), 8.18 (d, J=8.7 Hz, 1H), 8.04 (dd, J=4.8, 8.7 Hz), 7.87 (s, 1H), 7.76-7.52 (m, 5H), 7.46 (s, 2H), 7.11 (d, J=8.7 Hz, 1H), 5.35 (dd, J=12.3, 26.7 Hz, 1H), 5.19 (dd, J=11.7, 25.8 Hz, 1H), 4.26 (s, 2H), 2.75 (s, 3H).

Workup

  1. additionwas added to the reaction
  2. stirringstirred til precipitation
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a948eb9f0c604237b8e96fd8fa6d5870
Source dataset
uspto-grants-2015_02
Patent number
US08946273B2

Reaction notes

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