2-Naphthalenesulfonyl chloride → HCID 67727807, compound

HRID 963044Notes

Reaction equation

HRID 963044 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:23][CH2:24][C:25]1[N:29]([C:30]2[S:31][C:32]([CH2:44][CH3:45])=[CH:33][C:34]=2[C:35](=[O:43])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[Cl:42])[CH:28]=[N:27][N:26]=1.[CH:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][C:47]=1[S:56](Cl)(=[O:58])=[O:57].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[C:35]([C:34]1[CH:33]=[C:32]([CH2:44][CH3:45])[S:31][C:30]=1[N:29]1[CH:28]=[N:27][N:26]=[C:25]1[CH2:24][NH:23][S:56]([C:47]1[CH:48]=[CH:49][C:50]2[C:55](=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:46]=1)(=[O:58])=[O:57])=[O:43]

Participants

6

Reactant 4

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22439190HCID 22439190, compound

Product 1

HCID 67727807HCID 67727807, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazole di-p-toluenesulfonate (5.0 g) was dissolved in dimethylformamide (20 ml). 2-Naphthalenesulfonyl chloride (1.8 g) and triethylamine (5.0 ml) were added under ice-cooling, and the mixture was stirred at room temperature for 5 hours. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous citric acid solution and then saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from ethyl acetate to give 2.73 g of N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-3-ylmethyl)naphthalene-2-sulfonamide.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous citric acid solution
  4. dry with materialsaturated brine, and dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-058d8d7f6ea944788697a67dd2f74ca6
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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