4-Toluenesulfonyl chloride → 2-Amino-3-benzoyl-6-(4-methylphenylsulphonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 430625Notes

Reaction equation

HRID 430625 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClCCl>[NH2:1][C:2]1[S:10][C:5]2[CH2:6][N:7]([S:32]([C:29]3[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=3)(=[O:34])=[O:33])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 15434454(2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)phenylmethanone

Product 1

HCID 154344472-Amino-3-benzoyl-6-(4-methylphenylsulphonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well-stirred and ice-cooled solution of 2-amino-3-benzoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (0.78 mmol, 0.2 g) in dichloromethane (20 ml) under an argon atmosphere, was added triethylamine (0.162 ml) and then p-toluenesulfonyl chloride (0.93 mmol, 177 mg) portionwise. The suspension was stirred at room temperature for 24 h and the precipitated solid was filtered. The organic solution was evaporated under vacuum to give a solid residue which was chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture to afford 2-amino-3-benzoyl-6-(4-methylphenylsulphonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine. (m.p.165-167° C., 85 yield). 1 H-NMR (CDCl3): 1.95 (m, 2H); 2.43 (s, 3H); 3.07 (t, 2H); 3.51 (s, 2H); 6.76 (sb, 2H); 7.3-7.67 (m, 9H).

Workup

  1. stirringThe suspension was stirred at room temperature for 24 h
  2. filtrationthe precipitated solid was filtered
  3. customThe organic solution was evaporated under vacuum
  4. customto give a solid residue which
  5. customwas chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture

Sources & evidence

ORD record
ord-984ae31d032e4b31803493d828538331
Source dataset
uspto-grants-2001_11
Patent number
US06323214B1

Reaction notes

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