Sulfuric Acid → HCID 66699096, compound

HRID 1467830Notes

Reaction equation

HRID 1467830 reaction equation
[CH3:1][N:2]1[C:10]([CH2:11][C:12]([O:14]C)=[O:13])=[C:9]2[C:4]([N:5]([CH3:19])[C:6](=[O:18])[N:7]([CH3:17])[C:8]2=[O:16])=[N:3]1.OS(O)(=O)=O>O1CCOCC1.O>[CH3:1][N:2]1[C:10]([CH2:11][C:12]([OH:14])=[O:13])=[C:9]2[C:4]([N:5]([CH3:19])[C:6](=[O:18])[N:7]([CH3:17])[C:8]2=[O:16])=[N:3]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 123593308HCID 123593308, compound

Product 1

HCID 66699096HCID 66699096, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Step 6 intermediate (1.0 g, 3.755 mmol) and 6 N H2SO4 (9.3 ml) in dioxane (9.3 ml) stirred at reflux temperature for 2 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 330 mg of the product as a white solid; 1H NMR (300 MHz, DMSO-d6): δ 3.17 (s, 3H), 3.34 (s, overlapping with DMSO, 3H), 3.79 (s, 3H), 4.11 (s, 2H), 12.95 (br s, 1H) and 1H NMR (300 MHz, CDCl3): δ 3.39 (s, 3H), 3.50 (s, 3H), 3.88 (s, 3H), 4.10 (s, 2H).

Workup

  1. temperatureat reflux temperature for 2 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-3235beea83744c6f96c796ef43e3f461
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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