Water → N-(2-chloro-4-sulfamoyl-phenyl)-2-[[4-(8-ethyltetralin-5-yl)-5-(fluoromethyl)-1,2,4-triazol-3-yl]sulfanyl]acetamide

HRID 889421Notes

Reaction equation

HRID 889421 reaction equation
[CH2:1]([C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([N:13]2[C:17]([CH2:18][F:19])=[N:16][N:15]=[C:14]2[SH:20])=[CH:5][CH:4]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](=[O:41])(=[O:40])[NH2:39])=[CH:34][C:33]=1[Cl:42])=[O:30].O>CN(C=O)C>[Cl:42][C:33]1[CH:34]=[C:35]([S:38](=[O:41])(=[O:40])[NH2:39])[CH:36]=[CH:37][C:32]=1[NH:31][C:29](=[O:30])[CH2:28][S:20][C:14]1[N:13]([C:6]2[C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=3[C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[C:17]([CH2:18][F:19])=[N:16][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 215288302-chloro-N-(2-chloro-4-sulfamoylphenyl)acetamideHCID 178436513HCID 178436513, compound

Product 1

HCID 16728211N-(2-chloro-4-sulfamoyl-phenyl)-2-[[4-(8-ethyltetralin-5-yl)-5-(fluoromethyl)-1,2,4-triazol-3-yl]sulfanyl]acetamideYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a solution of 4-(4-ethyl-5,6,7,8-tetrahydro-naphthalen-1-yl)-5-fluoromethyl-4H-[1,2,4]triazole-3-thiol (85 mg, 0.29 mmol), K2CO3 (44.4 mg, 0.32 mmol) in DMF (2.0 mL) was added 2-chloro-N-(2-chloro-4-sulfamoyl-phenyl)-acetamide (82.6 mg, 0.29 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 (73.0 mg, 47% yield).

Workup

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

Sources & evidence

ORD record
ord-63760f899a5345aab58b990b6fef9a58
Source dataset
uspto-grants-2012_08
Patent number
US08252828B2

Reaction notes

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