Water → p-methyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]benzene-sulfonamide

HRID 1358316Notes

Reaction equation

HRID 1358316 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][C:6]1[C:7]([Cl:19])=[N:8][C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:10][C:11]=1Cl.[K+].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([NH-:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.O>CS(C)=O>[CH3:35][C:25]1[CH:26]=[CH:27][C:28]([S:31]([NH:34][C:11]2[C:6]([O:5][C:4]3[CH:20]=[CH:21][CH:22]=[CH:23][C:3]=3[O:2][CH3:1])=[C:7]([Cl:19])[N:8]=[C:9]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[N:10]=2)(=[O:33])=[O:32])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 111754584,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidineHCID 12228337p-Toluene-sulfonamide potassium salt

Product 1

HCID 11431637p-methyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]benzene-sulfonamideYield 68.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2 g 5-(o-methoxyphenoxy)-4,6-dichloro-2-(4-pyridyl)-pyrimidine was dissolved in 30 ml dry DMSO. 2.40 g p-toluene-sulfonamide potassium salt was added and stirring continued for 20 h. The reaction mixture was poured onto 200 ml water and extracted twice with 200 ml diethylether. The combined organic layers were extracted twice with 50 ml water. The combined water layers were acidified by acetic acid to pH=4. The precipitated product was filtered off, washed with ether and dried under reduced pressure. 1.9 g p-methyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]benzene-sulfonamide was obtained as a slightly colored solid. Rf (EA/Hex=1/1)=0.15.

Workup

  1. extractionextracted twice with 200 ml diethylether
  2. extractionThe combined organic layers were extracted twice with 50 ml water
  3. filtrationThe precipitated product was filtered off
  4. washwashed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0eb65fc3856a473ba48caf8de51c17ed
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

Loading…