Dimethylformamide → HCID 22139326, compound

HRID 1825750Notes

Reaction equation

HRID 1825750 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]([CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:7]([CH3:9])=[O:8].[OH-].[Na+].CN(C)[CH:24]=[O:25]>O>[NH:6]([CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:24]=[O:25])[C:7]([CH3:9])=[O:8]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22139217N-(1H-Indol-5-ylmethyl)acetamide

Product 1

HCID 22139326HCID 22139326, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus oxychloride (0.38 ml, 0.004 mol) was slowly added at 0° C. under nitrogen atmosphere to anhydrous N,N-dimethylformamide (1.9 ml, 0.025 mol). The mixture was stirred for 15 minutes and a solution of 5-acetamino methylindole (0.73 g, 0.0039 mol) in anhydrous N,N-dimethylformamide (4 ml) was added dropwise below 2° C. The mixture was stirred at room temperature for 3 h and diluted with an equal volume of water. The solution was neutralized (pH 8) with 1 N aqueous solution of sodium hydroxide. The mixture was evaporated to dryness under reduced pressure and the residue was recrystallized from ethyl acetate to afford 0.5 g (60%) of the entitled product (mp 182–184° C.).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6e23b597471a472c9d0d0a06ee405d6c
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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