Water → HCID 90258685, compound

HRID 1051200Notes

Reaction equation

HRID 1051200 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:2]1.[CH3:15][C:16]1([CH3:33])[O:20][CH:19]([CH2:21]OS(C2C=CC(Cl)=CC=2)(=O)=O)[CH2:18][O:17]1.CC(C)([O-])C.[Na+].O>O1CCOCC1>[CH3:15][C:16]1([CH3:33])[O:20][C@H:19]([CH2:21][N:1]2[CH:5]=[CH:4][C:3]([NH:6][C:7](=[O:14])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[N:2]2)[CH2:18][O:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 90258790HCID 90258790, compoundHCID 178522341HCID 178522341, compound

Product 1

HCID 90258685HCID 90258685, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

N-(1H-Pyrazol-3-yl)-benzamide (2.5 g, 20 mmol) and 4-Chloro-benzenesulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (6.75 g, 22 mmol) were dissolved in anhydrous 1,4-dioxane (30 ml). Sodium tert-butoxide (2.28 g, 23.8 mmol) was added in one portion at room temperature. The yellow suspension was heated to reflux with agitation for 23 hrs. The mixture was cooled to 10° C., water (80 ml) was added. The mixture was extracted with ethyl acetate (30 ml*2), the organic layer was washed with 1N NaOH (20 ml), 10% aqueous NaCl (40 ml*2). The organic layer was dried over Na2SO4, concentrated under reduced pressure to give the crude product as oil. Purified by silicon column (hexane/EA=5:1 to hexane/EA=3:1) to give off-white solid (3 g), yield: 50%. 1H-NMR (400 MHz, d6-DMSO): δ 10.86 (s, 1H), 7.99-8.01 (d, 2H), 7.67 (s, 1H), 7.47-7.58 (m, 3H), 6.63 (s, 1H), 4.4-4.42 (m, 1H), 4.16-4.38 (m, 2H), 4.01-4.05 (m, 1H), 3.75-3.78 (m, 1H), 1.33 (s, 3H), 1.25 (s, 3H).

Workup

  1. temperatureThe yellow suspension was heated
  2. temperatureto reflux with agitation for 23 hrs
  3. extractionThe mixture was extracted with ethyl acetate (30 ml*2)
  4. washthe organic layer was washed with 1N NaOH (20 ml), 10% aqueous NaCl (40 ml*2)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product as oil
  8. customPurified by silicon column (hexane/EA=5:1 to hexane/EA=3:1)

Sources & evidence

ORD record
ord-ac586c22c30e4a3b98f28421f83be281
Source dataset
uspto-grants-2016_07
Patent number
US09388168B2

Reaction notes

Loading…