Diethylamine → HCID 3936377, compound

HRID 2050782Notes

Reaction equation

HRID 2050782 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Cl[CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 3936377HCID 3936377, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 300 ml of toluene were dissolved 175.4 g of diethylamine and 152.5 g of chloromethylstyrene and the solution was heated to 60°-70° C. for 13 hours. As the reaction progressed, diethylamine hydrochloride precipitated. After filtering off the hydrochloride, the filtrate was washed with water, dried the layer containing toluene with sodium sulfate anhydride, concentrated, and after the addition of 1 g of di-tert-butylcatechol, the mixture was distilled under reduced pressure to provide 120.2 g of diethylaminomethylstyrene as a colorless liquid having a boiling point of 60° C./2 mm Hg.

Workup

  1. temperaturethe solution was heated to 60°-70° C. for 13 hours
  2. customdiethylamine hydrochloride precipitated
  3. filtrationAfter filtering off the hydrochloride
  4. washthe filtrate was washed with water
  5. customdried the layer
  6. additioncontaining toluene with sodium sulfate anhydride
  7. concentrationconcentrated
  8. additionafter the addition of 1 g of di-tert-butylcatechol
  9. distillationthe mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-14d2c1730c51476cbc56b6bcbcdaa27b
Source dataset
uspto-grants-1991_05
Patent number
US05015551

Reaction notes

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