Sodium Hydroxide → HCID 19744368, compound

HRID 2254182Notes

Reaction equation

HRID 2254182 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([CH:8]([CH2:21][CH2:22][CH2:23][CH3:24])[C:9]([NH:11][C:12]1[CH:20]=[C:19]2[C:15]([CH:16]=[CH:17][NH:18]2)=[CH:14][CH:13]=1)=[O:10])[CH3:7].[OH-].[Na+].CN(C)[C:29](=[O:31])[CH3:30]>>[C:29]([C:16]1[C:15]2[C:19](=[CH:20][C:12]([NH:11][C:9](=[O:10])[CH:8]([CH2:6][CH3:7])[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:14]=2)[NH:18][CH:17]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide2×HCID 14753006HCID 14753006, compound

Product 1

HCID 19744368HCID 19744368, compoundYield 80%

Procedure

1.9 g. of phosphorus oxychloride was slowly added to 1.48 g. of N,N-dimethylacetamide at 0° C. The mixture was allowed to attain room temperature and a solution of 1.0 g. 6-(2-ethylhexanamido)indole in 2 ml. N,N-dimethylacetamide was added. After 15 minutes the reaction solution was basified to pH 14 with 20% w/v sodium hydroxide solution, briefly heated under reflux, then cooled and extracted with ethyl acetate. The combined extracts were washed with water, then with brine, dried (MgSO4) and evaporated to give 0.93 g (80%) of 3-acetyl-6-(2-ethylhexanamido)indole (DD) as an orange powder; partial NMR: 2.5 (s, 3H), COCH3), 7.7 (d, 1H, H2 -indole), 9.8 (br, s, 1H, NH).

Workup

  1. customat 0° C
  2. customto attain room temperature
  3. temperaturebriefly heated
  4. temperatureunder reflux
  5. temperaturecooled
  6. extractionextracted with ethyl acetate
  7. washThe combined extracts were washed with water
  8. dry with materialwith brine, dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-8b94cd47696848c9ad5dc33de8dc0d4d
Source dataset
uspto-grants-1993_08
Patent number
US05234942

Reaction notes

Loading…