Triethylamine → HCID 54513699, compound

HRID 963404Notes

Reaction equation

HRID 963404 reaction equation
[CH3:1][N:2]([CH3:10])[CH:3]=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[C:21]([Cl:28])[CH:20]=1>C1(C)C=CC=CC=1>[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([C:4](=[CH:3][N:2]([CH3:10])[CH3:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:24])=[C:21]([Cl:28])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 155922074-Bromo-2-chlorobenzoyl chloride

Product 1

HCID 54513699HCID 54513699, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

30.2 g of ethyl 3-dimethylaminoacrylate and 29.3 ml of triethylamine are dissolved in 180 ml of toluene and boiled at reflux. At this temperature a solution of 53 g of 4-bromo-2-chloro-benzoyl chloride (U.S. Pat. No. 4,959,363) in 50 ml of toluene is added dropwise over 30 min. and the mixture is subsequently heated at reflux for a further 1 hr. The mixture is left to cool to room temperature and is stirred in an ice bath for a further 30 min. The suspension is filtered and the precipitated triethylamine hydrochloride is washed with 40 ml of ice-cold toluene. The filtrate is concentrated to half of its volume and then, for crystallization, diluted with 100 ml of hexane and stirred in an ice bath for 1 hr. 51.2 g (67%) of ethyl 2-(4-bromo-2-chloro-benzoyl)-3-dimethylaminoacrylate are obtained as colourless crystals. M.p. 100°-101°.

Workup

  1. temperatureat reflux
  2. temperaturethe mixture is subsequently heated
  3. temperatureat reflux for a further 1 hr
  4. waitThe mixture is left
  5. filtrationThe suspension is filtered
  6. washthe precipitated triethylamine hydrochloride is washed with 40 ml of ice-cold toluene
  7. concentrationThe filtrate is concentrated to half of its volume
  8. customfor crystallization
  9. additiondiluted with 100 ml of hexane
  10. stirringstirred in an ice bath for 1 hr

Sources & evidence

ORD record
ord-085fa8c5d0844df5aa5c49e9f398eaa7
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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