Triethylamine → 1-(10H-Phenothiazin-10-yl)propan-2-one

HRID 1032962Notes

Reaction equation

HRID 1032962 reaction equation
[OH:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CS(C)=O>[O:1]=[C:2]([CH3:18])[CH2:3][N:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[S:11][C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3775581-phenothiazin-10-ylpropan-2-olHCID 516892Sodium Bicarbonate

Product 1

HCID 127152711-(10H-Phenothiazin-10-yl)propan-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of the compound (1) (2.52 g, 9.79 mmol) obtained above and triethylamine (9.5 ml, 68 mmol) in dimethyl sulfoxide (25 ml) was added a solution of sulfur trioxide-pyridine complex (4.67 g, 29.3 mmol) in dimethyl sulfoxide (25 ml), and the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off, and thus obtained brown solid was purified by column chromatography on silica gel to give pale green needle-like crystals. Yield 1.93 g (77%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthus obtained brown solid was purified by column chromatography on silica gel
  6. customto give pale green needle-like crystals

Sources & evidence

ORD record
ord-568ffebc8a7c487bb66290a0a450aab6
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

Loading…