Water → HCID 53837304, compound

HRID 1701472Notes

Reaction equation

HRID 1701472 reaction equation
O.C([O-])(=O)C.[Na+].[CH3:7][N:8]([CH2:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)[CH3:9].[C:18](Cl)(=[O:22])[C:19]([CH3:21])=[CH2:20]>C(OCC)(=O)C.C(O)(=O)C>[CH3:9][N:8]([CH2:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])=[CH:13][CH:12]=1)[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 13528Methacryloyl chlorideHCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-HCID 517045Sodium Acetate2×

Product 1

HCID 53837304HCID 53837304, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 5 l three-necked flask were placed 1 l of water and 225.5 g. of sodium acetate. After dissolution of the sodium acetate with stirring, the resulting solution was cooled on an ice bath and 375 g. of p-dimethylaminomethylaniline and 400 ml of acetic acid were added thereto. The resulting mixture was cooled until the temperature became below 10° C. To the cooled mixture was added dropwise 287.4 g. of methacrylic acid chloride gradually to the extent that the temperature in the flask might not exceed 10° C. After completion of the dropwise addition, the stirring was continued for 30 minutes at the same temperature, followed by further stirring for 2 hours without the ice bath. To the reaction mixture thus obtained were added 500 ml of ethyl acetate and a solution of 400 g. of sodium hydroxide in 600 ml of water and the resulting mixture was extracted with ethyl acetate. After the extract was dried over anhydrous magnesium sulfate, the ethyl acetate was removed by distillation. The residue was dissolved in 300 ml of benzene and poured into 3.2 l of cooled n-hexane to precipitate the desired product. White crystal mp.(melting point): 65.5° C.

Workup

  1. customIn a 5 l three-necked flask were placed
  2. temperaturethe resulting solution was cooled on an ice bath
  3. temperatureThe resulting mixture was cooled until the temperature
  4. custombecame below 10° C
  5. additionTo the cooled mixture was added dropwise 287.4 g
  6. customexceed 10° C
  7. additionAfter completion of the dropwise addition
  8. customTo the reaction mixture thus obtained
  9. extractionof sodium hydroxide in 600 ml of water and the resulting mixture was extracted with ethyl acetate
  10. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  11. customthe ethyl acetate was removed by distillation
  12. dissolutionThe residue was dissolved in 300 ml of benzene
  13. additionpoured into 3.2 l of cooled n-hexane
  14. customto precipitate the desired product
  15. custom65.5° C.

Sources & evidence

ORD record
ord-ae4ec3c7831a409b96e59b4a930376db
Source dataset
uspto-grants-1980_03
Patent number
US04193800

Reaction notes

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