Sulfuric Acid → HCID 18536020, compound

HRID 412132Notes

Reaction equation

HRID 412132 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N+:22]([O-])=O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[NH2:22])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18536021HCID 18536021, compound

Product 1

HCID 18536020HCID 18536020, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product from Step A (2.07 g, 5.72 mmol) in 20 mL of ethanol was added stannous(II) chloride (4.32 g, 22.8 mmol). The solution was heated to 50° C. for 45 minutes hour, then cooled to room temperature. The solution was poured into 2 mL of concentrated sulfuric acid, then heated to 90° C. for 30 minutes. After cooling, the solution was concentrated in vacuo, basified with 20% NaOH solution, and extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product as a brown oil.

Workup

  1. temperaturecooled to room temperature
  2. temperatureheated to 90° C. for 30 minutes
  3. temperatureAfter cooling
  4. concentrationthe solution was concentrated in vacuo
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-765f6904da514c18bf4c8a8f52045ab6
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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