Triethylamine → HCID 22500439, compound

HRID 1815448Notes

Reaction equation

HRID 1815448 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])(=[O:13])=[O:12].C(N(CC)CC)C.N1C=CC=CC=1.S(=O)(=O)=O>CS(C)=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([CH2:14][CH2:15][CH2:16][CH:17]=[O:18])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 22500388HCID 22500388, compound

Product 1

HCID 22500439HCID 22500439, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of the product of step c (524 mg, 1.98 mmol) and triethylamine (0.829 ml, 5.96 mmol) in DMSO (10 ml) was added a solution of sulfur trioxide-pyridine (948 mg, 5.96 mmol) in DMSO (10 ml) and the reaction mixture stirred at ambient temperature for 15 minutes. The reaction mixture was poured into ice-water (150 ml) and then extracted thrice with ethyl acetate (60 ml). The combined organic phases were washed with aqueous citric acid (70 ml) and brine (70 ml), then dried over anhydrous sodium sulfate. The filtrate was evaporated at reduced pressure and the residue purified by flash column chromatography (2:1 ethyl acetate:hexane) to afford the title compound (457 mg, 88%). 1H NMR 9.75 (1H, s), 8.50 (1H, s), 8.05-7.65 (6H, m), 3.26-3.22 (2H, m), 2.71 (2H, t, 6.9), 2.15-2.04 (2H, m).

Workup

  1. extractionextracted thrice with ethyl acetate (60 ml)
  2. washThe combined organic phases were washed with aqueous citric acid (70 ml) and brine (70 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe filtrate was evaporated at reduced pressure
  5. customthe residue purified by flash column chromatography (2:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-8c2e915511de419fa2911a4550297d18
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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