Water → 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-isopropyl-benzenesulfonamide

HRID 2424378Notes

Reaction equation

HRID 2424378 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH:12]([CH3:14])[CH3:13])(=[O:10])=[O:9].[H-].[Na+].[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([Cl:25])=[CH:20][N:19]=1.O>CN1C(=O)N(C)CC1>[Cl:17][C:18]1[N:23]=[C:22]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([NH:11][CH:12]([CH3:14])[CH3:13])(=[O:10])=[O:9])[C:21]([Cl:25])=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2372592,4,5-TrichloropyrimidineHCID 167834652-Amino-N-isopropylbenzenesulfonamide

Product 1

HCID 587485602-(2,5-Dichloro-pyrimidin-4-ylamino)-N-isopropyl-benzenesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

To a solution of 2-amino-N-isopropyl-benzenesulfonamide (16.1 g, 75.1 mmol) in DMI (150 mL) is added sodium hydride (6.6 g, 165.3 mmol) portionwise at 0° C. After the mixture is stirred at room temperature for one hour, 2,4,5-trichloropyrimidine (20.7 g, 112.7 mmol) is added at 0° C. After further stirring at room temperature for 5 hrs, water is added and the mixture is extracted with AcOEt three times. Organic layer is washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue is purified by silica gel column chromatography (Hexane to Hexane:AcOEt=4:1) to afford the title compound as pale brown solid (10.2 g, 38%).

Workup

  1. stirringAfter further stirring at room temperature for 5 hrs
  2. extractionthe mixture is extracted with AcOEt three times
  3. washOrganic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (Hexane to Hexane:AcOEt=4:1)

Sources & evidence

ORD record
ord-9dd6e05045b94fb48af2fc30f10e7bd2
Source dataset
uspto-grants-2011_06
Patent number
US07964592B2

Reaction notes

Loading…