Benzoyl chloride → HCID 178483600, compound

HRID 435470Notes

Reaction equation

HRID 435470 reaction equation
CN/[C:3](=C\C)/[C:4]([O:6][CH3:7])=[O:5].C([N:12]([CH2:15][CH3:16])[CH2:13]C)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH3:7][O:6][C:4](=[O:5])[C:3]([C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[C:15]([NH:12][CH3:13])[CH3:16]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 60010764HCID 60010764, compound

Product 1

HCID 178483600HCID 178483600, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

193.5 g (1.5 moles) of methyl methylaminocrotonate is dissolved in 450 ml of toluene, and 166.7 g (1.65 moles) of triethylamine is added; while cooling at 0° to 5° C., 211 g (1.5 moles) (=174 ml) of benzoyl chloride is then dripped into this mixture. After the mixture has been stirred for 12 hours at 25° C., the precipitated triethylamine hydrochloride is filtered off and the toluene solution is extracted with water. After the toluene phase has been dried with Na2SO4, the residue is evaporated under reduced pressure and the solid which is obtained is recrystallized from a 4:1 mixture of ligroin and toluene. There is obtained 217 g (62%) of a white solid; m.p.: 75°-77° C.

Workup

  1. temperaturewhile cooling at 0° to 5° C.
  2. filtrationthe precipitated triethylamine hydrochloride is filtered off
  3. extractionthe toluene solution is extracted with water
  4. dry with materialAfter the toluene phase has been dried with Na2SO4
  5. customthe residue is evaporated under reduced pressure
  6. customthe solid which is obtained
  7. customis recrystallized from a 4:1 mixture of ligroin and toluene

Sources & evidence

ORD record
ord-2e66b5d8c221416687474ec9548cee69
Source dataset
uspto-grants-1983_08
Patent number
US04401821

Reaction notes

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