Triethylamine → 1727-53-3

HRID 1598643Notes

Reaction equation

HRID 1598643 reaction equation
[Br:1][CH:2]([CH:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]C)=[O:4].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Br:1][C:2](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 245160Methyl 2,3-dibromo-3-phenylpropanoate

Product 1

HCID 2465851727-53-3

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 50 g of methyl 2,3-dibromo-3-phenylpropanoate 1B, 100 ml of triethylamine and 500 ml of toluene is heated to boiling for 1 h, then cooled to room temperature and filtered. The filtrate is evaporated in vacuo and the α-bromocinnamic acid 1C thus obtained is reused without purification. 0.2 mol of imidazopyridine, dissolved in 150 ml of anhydrous DMF, is added dropwise with stirring to a suspension of 4.7 g of NaH (80% strength in mineral oil) in 100 ml of anhydrous DMF. During this process, the temperature of the mixture is kept below 35° C. by cooling with ice. After addition is complete, the mixture is stirred at room temperature for 1 h. The α-bromocinnamic acid previously prepared is dissolved in 200 ml of anhydrous DMF and the solution of the azole sodium salt is added dropwise with stirring while cooling with ice. After stirring at room temperature for 2 hours, 10.8 ml of glacial acetic acid are added, the mixture is stirred into 1.5 l of ice water and extracted several times with ethyl acetate, and the organic phases are washed with water. The organic phases are dried and evaporated in vacuo, and the residue is crystallized from ethyl acetate. 37.0 g of 1D are obtained as pale yellow crystals.

Workup

  1. temperatureis heated
  2. filtrationfiltered
  3. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-a9f0c58820a54f5492da86d70e5c5b1e
Source dataset
uspto-grants-1998_04
Patent number
US05739147

Reaction notes

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