Sulfuric Acid → HCID 18535988, compound

HRID 412126Notes

Reaction equation

HRID 412126 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[N+:22]([O-])=O)[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:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[NH2:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18536196HCID 18536196, compound

Product 1

HCID 18535988HCID 18535988, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product from Step A (7.69 g, 21.34 mmol) in 80 mL of ethanol was added stannous(II) chloride (20.17 g, 106.7 mmol). The solution was heated to 50° C. for one hour, then cooled to room temperature. The solution was poured into 10 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-060c12d0a4274f09b0838d43c463bead
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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