Triethylamine → HCID 86734580, compound

HRID 597453Notes

Reaction equation

HRID 597453 reaction equation
[Cl:1]/[C:2](/[CH3:7])=[CH:3]\[C:4](Cl)=[O:5].[NH2:8][C:9]1[CH:10]=[C:11]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])[CH:12]=[CH:13][CH:14]=1.C(N(CC)CC)C>O1CCCC1>[C:15]([C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[NH:8][C:4](=[O:5])/[CH:3]=[C:2](\[Cl:1])/[CH3:7])(=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1372881-(3-Aminophenyl)butan-1-oneHCID 12231244HCID 12231244, compound

Product 1

HCID 86734580HCID 86734580, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

29.2 g of β-chlorocrotonyl chloride were added over one hour at 0° C to a mixture of 31 g of m-amino-butyrophenone 21.2 g of triethylamine and 300 ml of tetrahydrofuran and after stirring for 16 hours at 20° C, the mixture was vacuum filtered. The filtrate was concentrated to dryness and the residue was chromatographed over silica gel to obtain 25 g of m-butyryl-3-chlorocrotonanilide melting at 106° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to dryness
  3. customthe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-9438bb52a6ca4506b808cc1c9347f1e7
Source dataset
uspto-grants-1977_03
Patent number
US04014679

Reaction notes

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