Acetic Acid → HCID 18914246, compound

HRID 1292410Notes

Reaction equation

HRID 1292410 reaction equation
[C:1](O)(=O)[CH3:2].[CH3:5][NH:6][CH3:7].[CH3:8][C:9]1[CH:10]=[C:11]([C:16]2[NH:17][C:18]3[C:23](C=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=[C:13]([CH3:15])[CH:14]=1>C(O)C>[CH3:8][C:9]1[CH:10]=[C:11]([C:16]2[NH:17][C:18]3[C:23]([C:1]=2[CH2:2][N:6]([CH3:7])[CH3:5])=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 674DimethylamineHCID 22100925HCID 22100925, compound

Product 1

HCID 18914246HCID 18914246, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.53 g glacial acetic acid was added 2.0 g dimethyl amine (40% aqueous solution) followed by 1.37 g fomalin (37% solution) then 4.0 g 2-(3,5-dimethylphenyl)-1H-indole and the mixture stirred at 0° C. After 15 minutes, 40 mL ethanol was added and the mixture allowed to warm to room temperature. After 1 hour at room temperature, the reaction was quenched by pouring into 50 mL of 1N sodium hydroxide. The resulting mixture was extracted with methylene chloride (4×10 mL) and the combined organics dried over potassium carbonate. Concentration in vacuo gave the crude title compound (4.15 g).

Workup

  1. waitAfter 1 hour at room temperature
  2. customthe reaction was quenched
  3. additionby pouring into 50 mL of 1N sodium hydroxide
  4. extractionThe resulting mixture was extracted with methylene chloride (4×10 mL)
  5. dry with materialthe combined organics dried over potassium carbonate
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-05611d4cc5ae4d98a4701afe01174273
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

Loading…