Water → HCID 18184184, compound

HRID 1358329Notes

Reaction equation

HRID 1358329 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([Cl:14])[N:5]=[C:4]([S:15][CH3:16])[N:3]=1.[K+].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH-:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].CCN(C(C)C)C(C)C.O>CS(C)=O>[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:2]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:6]([Cl:14])[N:5]=[C:4]([S:15][CH3:16])[N:3]=2)(=[O:29])=[O:30])=[CH:24][CH:23]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 6231014,6-Dichloro-2-methylthio-5-phenylpyrimidineHCID 131721323HCID 131721323, compound

Product 1

HCID 18184184HCID 18184184, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.77 g 4,6-dichloro-2-methylthio-5-phenylpyrimidine was dissolved in 50 ml DMSO and 3.42 g 4-tert-butylbenzenesulfonamide potassium salt and 1 ml Hünig's base was added. Stirring was continued for 24 h. The mixture was poured onto 400 ml water, washed with diethylether and acidified with conc. hydrochloric acid. The product precipitated and was filtered off and dried in vacuo to give 4 g of 4-tert.-butyl-N-(6-chloro-2-methylsulfanyl-5-phenyl-pyrimidin-4-yl)-benzenesulfonamide. LC-MS: tR=6.29 min, [M+1]+=448.17; 459.17.

Workup

  1. washwashed with diethylether
  2. customThe product precipitated
  3. filtrationwas filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f8cc91e8c25b4ba7bae754097f4d1979
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

Loading…