Dimethyl Sulfoxide → HCID 57022280, compound

HRID 442923Notes

Reaction equation

HRID 442923 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[C:9]([S:10]([O:13][C:14]3[CH:15]=[C:16]([CH:22]=[C:23]([CH3:25])[CH:24]=3)[O:17][CH2:18][CH2:19][CH2:20][OH:21])(=[O:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=12.C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[N:1]1[S:2][N:3]=[C:4]2[C:9]([S:10]([O:13][C:14]3[CH:15]=[C:16]([CH:22]=[C:23]([CH3:25])[CH:24]=3)[O:17][CH2:18][CH2:19][CH:20]=[O:21])(=[O:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 57049612HCID 57049612, compound

Product 1

HCID 57022280HCID 57022280, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (720 mg, 4.5 mmol) was added to a solution of 3-[3-(benzo-2,1,3-thiadiazole-4-sulfonyloxy)-5-methylphenoxy]propanol (565 mg, 1.5 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.6 mL, 4.7 mmol) and anhydrous dimethyl sulfoxide (0.3 mL, 4.2 mmol) in anhydrous dichloromethane (15 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (50 mL). The mixture was extracted into dichloromethane (3×50 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (40 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane) to give the title compound as a pale yellow oil (450 mg, 80%). 1H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1H), 8.35 (d, J=8.7 Hz, 1H), 8.27 (d, J=7.1 Hz, 1H), 7.72 (t, J=8.6 Hz, 1H), 6.59 (s, 1H), 6.49 (s, 1H), 6.44 (s, 1H), 4.17 (t, J=6.0 Hz, 2H), 2.85 (t, J=6.0 Hz, 2H), 2.21 (s, 3H).

Workup

  1. customquenched with 10% aqueous citric acid (50 mL)
  2. extractionThe mixture was extracted into dichloromethane (3×50 mL)
  3. washthe dichloromethane solution was washed with 10% aqueous citric acid (40 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-e23ed87e2c1c491f8885e79b1161f9aa
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

Loading…