Carbon Dioxide → HCID 12909166, compound

HRID 2395534Notes

Reaction equation

HRID 2395534 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][NH:15][CH3:16].[C:17](=O)=O>C=O>[CH3:14][N:15]([CH2:17][C:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[CH2:11])[CH3:16]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 674DimethylamineHCID 4661(4-Nitrophenyl)acetic acid

Product 1

HCID 12909166HCID 12909166, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent2×

Conditions

Temperature
10 °C

Procedure

The compound 4-nitrophenylacetic acid (30.2 g, 0.166 mole) was dissolved in 210 ml (1.7 mole) of 33% aqueous dimethylamine solution and cooled to 10° C. in an ice bath. Immediately to the reaction solution was added dropwise 150 ml of 38% aqueous formaldehyde solution, under a nitrogen atmosphere, while maintaining the temperature between 15°-20° C. When the addition of the formaldehyde was complete, the reaction mixture was stirred for 0.5 hours at 20° C., then for 0.5 hours with warming to 60° C. (evolving carbon dioxide), and then for 10 hours at room temperature. The light yellow oil, which separated from solution, was taken up in 3×30 ml portions of chloroform. The chloroform layer was extracted with 3×30 ml portions of 3N hydrochloric acid. Upon neutralization with saturated potassium bicarbonate solution an oily layer was separated, extracted with 3×30 ml portions of chloroform, washed with an equal volume of saturated sodium chloride solution, and dried over anhydrous Na2SO4. Evaporation of the chloroform provided 31.5 g (93%) of crude α-(N,N-dimethylaminomethyl)-p-nitrostyrene.

Workup

  1. temperatureunder a nitrogen atmosphere, while maintaining the temperature between 15°-20° C
  2. waitfor 10 hours at room temperature
  3. customThe light yellow oil, which separated from solution
  4. extractionThe chloroform layer was extracted with 3×30 ml portions of 3N hydrochloric acid
  5. customUpon neutralization with saturated potassium bicarbonate solution an oily layer was separated
  6. extractionextracted with 3×30 ml portions of chloroform
  7. washwashed with an equal volume of saturated sodium chloride solution
  8. dry with materialdried over anhydrous Na2SO4
  9. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-5b2a9514b9bc44b4a0bcc1ea3da54c45
Source dataset
uspto-grants-1996_02
Patent number
US05489425

Reaction notes

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