Pyridine → HCID 56966002, compound

HRID 1036933Notes

Reaction equation

HRID 1036933 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[NH2:15])[CH2:3]1.N1C=CC=CC=1.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl.O>[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[NH:15][S:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:35])=[O:34])[CH2:3]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 67291611HCID 67291611, compound

Product 1

HCID 56966002HCID 56966002, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-2-yl)aniline (150 mg, 0.56 mmol) and pyridine (0.5 mL) in dichloromethane (2 mL) was added benzenesulfonyl chloride (72 μL) at ice-bath under nitrogen. After addition, the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Sodium sulfate, removed the solvent under reduced pressure, the residue was purified by HPLC to give N-[2-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-benzensulfonamide LC/MS m/e obsd. (ESI+) [(M+H)+] 407.3.

Workup

  1. additionAfter addition
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous Sodium sulfate
  4. customremoved the solvent under reduced pressure
  5. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-37da53b08962496883ee0ee70cc8face
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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