Dimethylformamide → HCID 19832360, compound

HRID 2051538Notes

Reaction equation

HRID 2051538 reaction equation
[CH3:1][C:2]1([CH3:21])[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:20].CI.[C:24](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:24][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]([NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[CH:6]=2)[C:2]([CH3:21])([CH3:1])[C:3]1=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 146240562,3-Dihydro-3,3-dimethyl-N-phenyl-2-oxo-(1H)-indole-6-carboxamide

Product 1

HCID 19832360HCID 19832360, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.8 g. (10 mmol) 2,3-Dihydro-3,3-dimethyl-N-phenyl-2-oxo-(1H)-indole-6-carboxamide, 2.8 g. (20 mmol) methyl iodide and 2.5 g. (20 mmol) potassium carbonate were stirred in 50 ml. dimethylformamide for 3 hours at 70° C. After cooling, the reaction mixture was mixed with water, decanted and again mixed with water. The residue was purified by column chromatography (RP-18, methanol:water:ammonium hydroxide 80:20:1 v/v/v). Pure fractions were evaporated until the commencement of crystallisation, subsequently filtered off with suction and washed with water. There were obtained 2.3 g. (78% of theory) of the title compound; m.p. 184-186° C.

Workup

  1. temperatureAfter cooling
  2. customdecanted
  3. additionagain mixed with water
  4. customThe residue was purified by column chromatography (RP-18, methanol:water:ammonium hydroxide 80:20:1 v/v/v)
  5. customPure fractions were evaporated until the commencement of crystallisation
  6. filtrationsubsequently filtered off with suction
  7. washwashed with water
  8. customThere were obtained 2.3 g

Sources & evidence

ORD record
ord-e2b31e1a86244ebab9e739da38ac6e8e
Source dataset
uspto-grants-1991_05
Patent number
US05019587

Reaction notes

Loading…