Triethylamine → HCID 86621239, compound

HRID 1594380Notes

Reaction equation

HRID 1594380 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([NH:14][CH:15]=[O:16])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Br:13])[CH3:2].[Br:18]N1C(=O)CCC1=O.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[C:5]([NH:14][CH:15]=[O:16])=[C:6]([Br:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Br:13])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 86621240HCID 86621240, compound

Product 1

HCID 86621239HCID 86621239, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0.4 M solution of 3-(2-bromo-phenyl)-2-formylamino-acrylic acid ethyl ester (5.3 g; 17.8 mM) in anhydrous CH2Cl2, at 0° C., is added with N-bromosuccinimide (3.48 g; 19.6 mM). The mixture is left to slowly warm to room temperature. The reaction is completed in about 5 hours 30 mm. The equivalent amount of triethylamine is added drop by drop; after 30 minutes the mixture is washed with a NaHCO3 saturated solution and then with a NaCl saturated solution. The organic phase is dried over Na2SO4, the solid is filtered off and the clear solution is evaporated under reduced pressure to a residue. The crude (brownish oil) is purified by flash chromatography, using a 6:4 v/v mixture of hexane and ethyl acetate as eluent, thereby obtaining 2.68 g of 3-bromo-3-(2-bromo-phenyl)-2-formylamino-acrylic acid ethyl ester (white-pale yellow solid). (Yield: 40%).

Workup

  1. waitThe mixture is left
  2. washafter 30 minutes the mixture is washed with a NaHCO3 saturated solution
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationthe solid is filtered off
  5. customthe clear solution is evaporated under reduced pressure to a residue
  6. customThe crude (brownish oil) is purified by flash chromatography
  7. additiona 6:4 v/v mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-07359ccf0fb5470d85222ba37c7da62b
Source dataset
uspto-grants-2007_11
Patent number
US07301027B2

Reaction notes

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