4-Toluenesulfonyl chloride → HCID 56966429, compound

HRID 1036976Notes

Reaction equation

HRID 1036976 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:20])[CH3:19].[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([NH:18][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67290361HCID 67290361, compound

Product 1

HCID 56966429HCID 56966429, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(6-Chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (150 mg, 0.53 mmol) and 4-methyl-benzenesulfonyl chloride (103 mg, 0.63 mmol) were dissolved in pyridine (5 ml). The mixture was stirred at room temperature overnight. The solvent was removed and the residue was purified on column chromatography using petroleum ether/Ethyl acetate=5:1 as eluent to afford N-[3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-4-methyl-benzenesulfonamide (133 mg, yield: 46%) as yellow solid. MS (ESI+APCI) M+1=441.1.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on column chromatography

Sources & evidence

ORD record
ord-1d37c87e27cb4e769e48270efd16939f
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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