Sulfuric Acid → HCID 67042319, compound

HRID 1929284Notes

Reaction equation

HRID 1929284 reaction equation
C([NH:4][C:5]1[C:6]([N+:17]([O-:19])=[O:18])=[C:7]([CH:13]=[CH:14][C:15]=1[Cl:16])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=O)C.S(=O)(=O)(O)O>C(O)C>[NH2:4][C:5]1[C:6]([N+:17]([O-:19])=[O:18])=[C:7]([CH:13]=[CH:14][C:15]=1[Cl:16])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67041619HCID 67041619, compound

Product 1

HCID 67042319HCID 67042319, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

138.63 g of the mixture from step 3 were dissolved in 1.4 l of ethanol and 60 ml of concentrated sulfuric acid and the solution was boiled at reflux for 25 h. Then 1.3 l of ethanol were removed on a rotary evaporator and the residue was admixed with 1 l of ice-water, rendered basic using saturated NaHCO3 solution, and then extracted with three times 500 ml of dichloromethane. The combined organic phases were dried over MgSO4, filtered with suction over silica gel, and concentrated. The product was then subjected to chromatographic separation (silica gel, heptane/ethyl acetate 9:1).

Workup

  1. temperatureat reflux for 25 h
  2. customThen 1.3 l of ethanol were removed on a rotary evaporator
  3. extractionextracted with three times 500 ml of dichloromethane
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered with suction over silica gel
  6. concentrationconcentrated
  7. customThe product was then subjected to chromatographic separation (silica gel, heptane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-265033eb295b46c8a93a496e25c01c7a
Source dataset
uspto-grants-2012_05
Patent number
US08188002B2

Reaction notes

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