Benzenesulfonyl chloride → HCID 18929758, compound

HRID 1598578Notes

Reaction equation

HRID 1598578 reaction equation
I.[N:2]1[NH:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]=1[C:8]1[S:12][C:11]2[CH2:13][CH2:14][CH:15]([NH2:17])[CH2:16][C:10]=2[CH:9]=1.C(N(CC)CC)C.[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN1CCN(C)C1=O>[N:2]1[NH:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]=1[C:8]1[S:12][C:11]2[CH2:13][CH2:14][CH:15]([NH:17][S:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:34])=[O:33])[CH2:16][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 18929750HCID 18929750, compound

Product 1

HCID 18929758HCID 18929758, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

To 1.34 g of 2-[4,5-dihydropyridazin-3(2H)-on-6-yl]-5-amino-4,5,6,7-tetrahydrobenzo[b]thiophene.hydroiodide and 1.2 ml of triethylamine dissolved in 20 ml of 1,3-dimethyl-2-imidazolidinone was added 765 mg of benzenesulfonyl chloride, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. After the organic layer was washed and dried, the solvent was removed. The resulting crystals were recrystallized from nitromethane to obtain 1.22 g of 2-[4,5-dihydropyridazin-3(2H)-on-6-yl]-5-(phenylsulfonylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed
  3. customdried
  4. customthe solvent was removed
  5. customThe resulting crystals were recrystallized from nitromethane

Sources & evidence

ORD record
ord-dba9202ba71f40febfc52f262d392cf8
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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