Water → HCID 15524337, compound

HRID 1976695Notes

Reaction equation

HRID 1976695 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)=[O:4].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CS(C)=O>[CH2:15]([NH:22][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)=[O:4])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 15524338HCID 15524338, compound

Product 1

HCID 15524337HCID 15524337, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution containing 2-chloro-N-(1H-indol-4-yl)-acetamide (3.0 g, 14.4 mmol), benzylamine (4.76 g, 43.1 mmol) in DMSO (60 mL) was stirred at ambient temperature for 16 hours. The mixture was poured into water (700 mL) and the crude product crystallized as a solid. After filtration, the solids were dissolved in ethyl acetate (600 mL), washed with water (200 mL) and brine (200 mL), dried over anhydrous magnesium sulfate and filtered. Concentration of the ethyl acetate gave the title compound as a white solid, (3.36 g, 83.6%), mp 158-161° C.; MS EI m/e 279 (M+).

Workup

  1. customthe crude product crystallized as a solid
  2. filtrationAfter filtration
  3. dissolutionthe solids were dissolved in ethyl acetate (600 mL)
  4. washwashed with water (200 mL) and brine (200 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-403c8b7093c247bcbec9d2cd5c451fa0
Source dataset
uspto-grants-2001_05
Patent number
US06228880B1

Reaction notes

Loading…