Pyridine → 4-(4-Chloro-phenoxy)-N-(2,5-dibromo-pyridin-3-yl)-benzenesulfonamide

HRID 1716280Notes

Reaction equation

HRID 1716280 reaction equation
[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([O:15][C:16]2[CH:17]=[CH:18][C:19]([S:22]([NH:8][C:7]3[C:2]([Br:1])=[N:3][CH:4]=[C:5]([Br:9])[CH:6]=3)(=[O:24])=[O:23])=[CH:20][CH:21]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27577504-(4-Chlorophenoxy)benzene-1-sulfonyl chlorideHCID 193875322,5-Dibromopyridin-3-amine

Product 1

HCID 866199334-(4-Chloro-phenoxy)-N-(2,5-dibromo-pyridin-3-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,5-dibromo-3-aminopyridine (0.51 g, 2.0 mmol) and 4-(4-chloro-phenoxy)-benzenesulfonyl chloride (0.76 g, 2.0 mmol) in dry CH2Cl2 (10 mL) was added pyridine (1 mL) at 0 C. The resulting mixture was allowed to warm to room temperature and stirred until TCL showed the completion of the reaction. The reaction mixture was diluted with CH2Cl2 and washed with aqueous HCl solution. After the pyridine was neutralized, the organics were washed with water, brine and dried over anhydrous Na2SO4. The filtration (Celite) and concentration under vacuo gave a crude material, which was purified by silica column (30% EtOAc/hexanes). MS: 516, 518 (M+H)+.

Workup

  1. customthe completion of the reaction
  2. washwashed with aqueous HCl solution
  3. washthe organics were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThe filtration (Celite) and concentration under vacuo

Sources & evidence

ORD record
ord-d44ecc8be2504abf90045b8b7f55bda9
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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