2,4-Dichloro-5-methylbenzene-1-sulphonyl chloride → N-[3-Chloro-5-fluoro-4-(quinolin-3-yloxy)phenyl]-2,4-dichloro-5-methyl-benzenesulfonamide

HRID 2422423Notes

Reaction equation

HRID 2422423 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[C:6]([F:19])[C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[C:25]([CH3:29])=[CH:24][C:23]=1[S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:20][S:30]([C:23]2[CH:24]=[C:25]([CH3:29])[C:26]([Cl:28])=[CH:27][C:22]=2[Cl:21])(=[O:32])=[O:31])[CH:5]=[C:6]([F:19])[C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 1199142,4-Dichloro-5-methylbenzene-1-sulphonyl chlorideHCID 221488123-Chloro-5-fluoro-4-(quinolin-3-yloxy)phenylamine

Product 1

HCID 22148901N-[3-Chloro-5-fluoro-4-(quinolin-3-yloxy)phenyl]-2,4-dichloro-5-methyl-benzenesulfonamideYield 73.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-chloro-5-fluoro-4-(quinolin-3-yloxy)phenylamine (50.2) (0.420 g) in pyridine (2.2 mL), was added 2,4-dichloro-5-methylbenzenesulfonylchloride 0.360 g. The mixture was stirred at room for 1 h. The reaction mixture was purified directly by column chromatography (silica gel, AcOEt:hexane=1:3). The product was triturated by hexane to give title compound (0.522 g). Yield 73% as a solid. 1H NMR (300 MHz/CDCl3) δ 2.43 (3H, s), 7.05 (1H, d, J=2.6 Hz), 7.09-7.11 (1H, m), 7.21 (1H, d, J=2.6 Hz), 7.36 (1H, brs), 7.49-7.66 (4H, m), 7.96 (1H, s), 8.10 (1H, d, J=8.2 Hz), 8.80 (1H, brs). MS (M+H) 511. mp 187° C.

Workup

  1. customThe reaction mixture was purified directly by column chromatography (silica gel, AcOEt:hexane=1:3)
  2. customThe product was triturated by hexane

Sources & evidence

ORD record
ord-7f71b1f0cb5247baadd8140c1d30d3f2
Source dataset
uspto-grants-2011_06
Patent number
US07960408B2

Reaction notes

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