Hydrochloric Acid → HCID 53684414, compound

HRID 1447200Notes

Reaction equation

HRID 1447200 reaction equation
CCN(C1C=CC=CC=1)CC.Cl[C:13]([O:15][CH3:16])=[O:14].[CH3:17][C:18]([CH3:25])=[CH:19][CH:20]=[N:21][CH:22]([CH3:24])[CH3:23].Cl>C1(C)C=CC=CC=1.O>[CH3:16][O:15][C:13](=[O:14])[N:21]([CH:22]([CH3:24])[CH3:23])[CH:20]=[CH:19][C:18]([CH3:25])=[CH2:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 7061N,N-DiethylanilineHCID 13061751HCID 13061751, compound

Product 1

HCID 53684414HCID 53684414, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 657 g diethylaniline in 2 liter toluene is added dropwise over ca. 5 minutes 416 g methyl chloroformate. Then to the stirred mixture 500 g N-(3-methyl-2-butenyliden)-isopropylamine in 500 ml toluene is added dropwise over 2 hours, maintaining the temperature between 25° and 30° C. Stirring is continued for 1 hour upon completion of the addition and the reaction mixture is treated with 400 ml of water and 90 ml conc. hydrochloric acid. The organic phase is washed with 600 ml of saturated aqueous sodium bicarbonate solution and with 600 ml water, dried and evaporated in vacuo to give the heading compound.

Workup

  1. temperaturemaintaining the temperature between 25° and 30° C
  2. additionis continued for 1 hour upon completion of the addition
  3. washThe organic phase is washed with 600 ml of saturated aqueous sodium bicarbonate solution and with 600 ml water
  4. customdried
  5. customevaporated in vacuo
  6. customto give the heading compound

Sources & evidence

ORD record
ord-efc4a1e9a62b42598dca9797fa9dc3c5
Source dataset
uspto-grants-1982_02
Patent number
US04316042

Reaction notes

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