Benzenesulfonyl chloride → N-(1-Benzenesulfonyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

HRID 1643902Notes

Reaction equation

HRID 1643902 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH:6]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:5]2.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[C:22]1([S:28]([N:8]2[C:9]3[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=3)[CH2:5][CH:6]([NH:12][S:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)(=[O:14])=[O:15])[CH2:7]2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 18177113N-(6-Bromo-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

Product 1

HCID 59778145N-(1-Benzenesulfonyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamideYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 87A (98 mg, 0.299 mmol) in pyridine (3 mL) was added benzenesulfonyl chloride (0.042 mL, 0.33 mmol). The mixture was stirred at RT overnight, then concentrated. The residue was chromatographed (10 g silica gel) eluting with EtOAc (0-60%) in hexane to give the title compound (140 mg, 93%) as a white foam. HPLC: 99% at 7.06 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 529 [M+Na]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was chromatographed (10 g silica gel)
  3. washeluting with EtOAc (0-60%) in hexane

Sources & evidence

ORD record
ord-5530bb27f8f643df927ca663963f44f9
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

Loading…