Triethylamine → 4-(Diethylamino)-1,3-diphenylbut-3-ene-1,2-dione

HRID 917812Notes

Reaction equation

HRID 917812 reaction equation
[CH2:1]([N:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.[C:21]1([C:27](=[O:31])[C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)C>[CH2:1]([N:3]([CH2:4][CH3:5])[CH:6]=[C:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:28](=[O:29])[C:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:31])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110842942-Oxo-2-phenylacetyl chlorideHCID 12773281Diethylstyrylamine

Product 1

HCID 539328324-(Diethylamino)-1,3-diphenylbut-3-ene-1,2-dione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Seven grams of N,N-diethylstyrylamine was dissolved in 100 ml. of diethyl ether and the solution was cooled to 0°C. Four grams of anhydrous triethylamine was added. A 7 g. portion of phenylglyoxyloyl chloride was dissolved in 50 ml. of diethyl ether and the solution was added dropwise, with stirring, to the first solution over about 75 minutes. As soon as the addition was complete, the reaction mixture was filtered, and the precipitated amine hydrochloride was washed with an additional 50 ml. of diethyl ether. The filtrate contained the intermediate enamine, 1-diethylamino-2,4-diphenyl-1-buten-3,4-dione, in dissolved form, and was used in the next step of the synthesis without purification.

Workup

  1. additionAs soon as the addition
  2. filtrationthe reaction mixture was filtered
  3. washthe precipitated amine hydrochloride was washed with an additional 50 ml
  4. customin dissolved form, and was used in the next step of the synthesis without purification

Sources & evidence

ORD record
ord-15a46dce46ed4d6ab5b8424b2a9a9ee7
Source dataset
uspto-grants-1976_07
Patent number
US03967952

Reaction notes

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