Sulfuric Acid → HCID 71007982, compound

HRID 877016Notes

Reaction equation

HRID 877016 reaction equation
[CH3:1][N:2]1[C:7]2[S:8][CH:9]=[C:10]([CH2:11][C:12]([O:14]C)=[O:13])[C:6]=2[C:5](=[O:16])[N:4]([CH3:17])[C:3]1=[O:18].OS(O)(=O)=O>O1CCOCC1.O>[CH3:1][N:2]1[C:7]2[S:8][CH:9]=[C:10]([CH2:11][C:12]([OH:14])=[O:13])[C:6]=2[C:5](=[O:16])[N:4]([CH3:17])[C:3]1=[O:18]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 131732594HCID 131732594, compound

Product 1

HCID 71007982HCID 71007982, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Step 9 intermediate (1.3 g, 4.850 mmol) and 6 N H2SO4 (12 ml) in 1,4-dioxane (12 ml) was stirred at reflux temperature for 1 h to give a homogeneous pale yellow solution. This solution was cooled, diluted with water and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with water, dried over Na2SO4 and concentrated. The residue obtained was triturated in diethyl ether, solid obtained was collected by filtration to give 450 mg of the product as a white solid; 1H NMR (DMSO-d6, 300 MHz) δ 3.21 (s, 3H), 3.45 (s, 3H), 3.79 (s, 2H), 7.01 (s, 1H), 12.22 (br s, 1H).

Workup

  1. temperatureat reflux temperature for 1 h
  2. customto give a homogeneous pale yellow solution
  3. temperatureThis solution was cooled
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customwas triturated in diethyl ether
  10. customsolid obtained
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-972b9bb089564736bde8bbb1dcf59ff1
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

Loading…