Dimethylformamide → HCID 22139226, compound

HRID 1825751Notes

Reaction equation

HRID 1825751 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH3:20])[S:8]([C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][NH:17]2)=[CH:13][CH:12]=1)(=[O:10])=[O:9].[OH-].[Na+].CN(C)[CH:25]=[O:26]>O>[CH3:6][N:7]([CH3:20])[S:8]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:25]=[O:26])=[CH:16][NH:17]2)=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 5323783HCID 5323783, compound

Product 1

HCID 22139226HCID 22139226, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus oxychloride (0.76 ml, 0.008 mol) was slowly added at 0° C. under nitrogen atmosphere to anhydrous N,N-dimethyl formamide (3.8 ml), 0.05 mol). The mixture was stirred for 15 minutes and a solution of 6-(N,N-dimethyl aminosulfonyl)indole (1.74 g, 0.0078 mol) in anhydrous N,N-dimethylformamide (4 ml) was added dropwise below 2° C. The reaction mixture was allowed to stand at room temperature for 20 h and diluted with water (10 ml). The solution was neutralized (pH 8) with 10% aqueous solution of sodium hydroxide. The mixture was cooled and the precipitated solid was collected by filtration and was recrystallized from ethanol to yield 1.05 g (54%) of the entitled product (mp 250–252° C.).

Workup

  1. waitto stand at room temperature for 20 h
  2. temperatureThe mixture was cooled
  3. filtrationthe precipitated solid was collected by filtration
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-b17fb418357d457995c591c2b8f08c69
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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