Hydrochloric Acid → n-Propanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide

HRID 2252723Notes

Reaction equation

HRID 2252723 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.[K+].[CH2:17]([S:20]([NH-:23])(=[O:22])=[O:21])[CH2:18][CH3:19].Cl>CS(C)=O>[Cl:15][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:23][S:20]([CH2:17][CH2:18][CH3:19])(=[O:22])=[O:21])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidineHCID 131726746n-Propanesulfonamide potassium salt

Product 1

HCID 86597589n-Propanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amideYield 78.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4,6-dichloro-5-(p-tolyl)pyrimidine (Example 1b; 717 mg) in DMSO (5 ml) and n-propanesulfonamide potassium salt (1016 mg) was added. Stirring was continued for 14 h at rt. The solution was poured onto ice/water and acidified by 2 N HCl to pH 3-4. The precipitate was filtered off and washed with water and diethylether to give n-propanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (765 mg) as a white powder. LC-MS: tR: 4.44, [M+H]+: 326.13.

Workup

  1. additionThe solution was poured onto ice/water
  2. filtrationThe precipitate was filtered off
  3. washwashed with water and diethylether

Sources & evidence

ORD record
ord-450a1559b8054087a94b1015001ff090
Source dataset
uspto-grants-2008_01
Patent number
US07323465B2

Reaction notes

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