Acetyl chloride → HCID 20136554, compound

HRID 579760Notes

Reaction equation

HRID 579760 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH:8]2[C:20](=[O:21])[C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH:4]=[CH:5][N:6]=1.[H-].[Na+].[H][H].[C:26](Cl)(=[O:28])[CH3:27]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[C:26]([N:12]1[C:11]2[CH2:10][CH2:9][CH:8]([CH2:7][N:3]3[CH:4]=[CH:5][N:6]=[C:2]3[CH3:1])[C:20](=[O:21])[C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 108912241,2,3,9-Tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 20136554HCID 20136554, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one (0.5 g) and 80% sodium hydride dispersion in mineral oil (0.07 g) in dry dimethylformamide (10 ml) was stirred under nitrogen until hydrogen evolution had ceased (ca. 0.5 h). The mixture was cooled to 0° and acetyl chloride (0.18 g) was added. The mixture was stirred at 0° for 1 h, diluted with 8% aqueous sodium bicarbonate (50 ml) and extracted with dichloromethane (2×50 ml). The dried (Na2SO4) extracts were evaporated to give a solid which was purified by flash chromatography (C) to give a solid (0.25 g). Recrystallisation from ethyl acetate-methanol afforded the title compound as crystals (0.12 g) m.p. 173°-175°.

Workup

  1. custom(ca. 0.5 h)
  2. temperatureThe mixture was cooled to 0°
  3. extractionextracted with dichloromethane (2×50 ml)
  4. dry with materialThe dried (Na2SO4) extracts
  5. customwere evaporated
  6. customto give a solid which
  7. customwas purified by flash chromatography (C)

Sources & evidence

ORD record
ord-2e188da554e8496081949c854f1566fa
Source dataset
uspto-grants-1988_06
Patent number
US04749718

Reaction notes

Loading…