Dimethylformamide → HCID 20222531, compound

HRID 980400Notes

Reaction equation

HRID 980400 reaction equation
CC1C=CC(S([CH:11]([C:24]2[N:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH3:22])[C:13]=2[CH3:23])(=O)=O)=CC=1.[OH-].[Na+].[CH3:32][N:33](C)[CH:34]=O>>[CH3:32][N:33]([CH:11]([C:24]1[N:25]([CH3:29])[CH:26]=[CH:27][CH:28]=1)[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH3:22])[C:13]=1[CH3:23])[CH3:34]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 13750810HCID 13750810, compound

Product 1

HCID 20222531HCID 20222531, compound

Procedure

A mixture containing 1.4 g. of 3-[(4-methylphenylsulfonyl)(1-methyl-2-pyrrolyl)methyl]-1-ethyl-2-methyl-1H-indole, 5 ml. of N,N-dimethylformamide and 30 ml. of 20% aqueous sodium hydroxide was heated 3 hours at 50° C. The reaction mixture was then cooled and diluted with 100 ml. of water and the product extracted with toluene. The toluene extracts were washed with water and evaporated to dryness affording 3-[(dimethylamino)(1-methyl-2-pyrrolyl)methyl]-1-ethyl-2-methyl-1H-indole as a brown gummy material, the infrared and nuclear magnetic resonance spectra of which were consistent with the assigned structure. A toluene solution of this product when contacted with acidic clay or phenolic resin developed an orange image.

Workup

  1. additionA mixture containing 1.4 g
  2. temperatureThe reaction mixture was then cooled
  3. additiondiluted with 100 ml
  4. extractionof water and the product extracted with toluene
  5. washThe toluene extracts were washed with water
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-cf39722bd297412ca82bee77eb9d4184
Source dataset
uspto-grants-1987_01
Patent number
US04636820

Reaction notes

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