Sulfuric Acid → HCID 13603942, compound

HRID 1085199Notes

Reaction equation

HRID 1085199 reaction equation
S(=O)(=O)(O)O.N[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:21])[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=1.N([O-])=[O:23].[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2]>[OH:23][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:21])[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 12561714HCID 12561714, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13603942HCID 13603942, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent4×

Procedure

To a solution of 350 g concentrated sulfuric acid and 350 ml of water, cooled to 0°, 40 g of ethyl 4-(4-aminophenyl)pentanoate was added dropwise, maintaining the temperature at 0°-2°. The mixture was treated dropwise with a solution of 13.66 g of sodium nitrite in 25 ml of water at a rate such that the temperature did not exceed 2°. The solution was added dropwise to a refluxing solution of 387 g of copper sulfate in 600 ml of water over a period of about 30 min and the resultant mixture was heated under reflux for an additional 10 min. The mixture was cooled to room temperature, 800 ml of water was added, and extracted thrice with dichloromethane (additional water was needed to dissolve the salts). The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and evaporated. The residue was distilled at 129° (0.6 mm) to give 21.05 g (53%) of product, mp 32°-34°.

Workup

  1. temperaturemaintaining the temperature at 0°-2°
  2. customdid not exceed 2°
  3. temperatureunder reflux for an additional 10 min
  4. extractionextracted thrice with dichloromethane (additional water
  5. dissolutionto dissolve the salts)
  6. washThe organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residue was distilled at 129° (0.6 mm)

Sources & evidence

ORD record
ord-1ad02c8323bf41b496edfcb3e0b72371
Source dataset
uspto-grants-1991_04
Patent number
US05008285

Reaction notes

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