Bromide ion → HCID 21163315, compound

HRID 2113894Notes

Reaction equation

HRID 2113894 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[Br-]>C(OCC)(=O)C>[CH3:20][O:19][C:17](=[O:18])[C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 6115AnilineHCID 7748Ethyl bromoacetateHCID 8471Triethylamine

Product 1

HCID 21163315HCID 21163315, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of aniline, triethyl amine, and ethyl bromoacetate was heated to 60° C. for 2.5 days. The reaction mixture was cooled, and TLC (25% EtOAc/hex) showed mostly starting material and a higher Rf spot. Additional base, bromide, and continued heat for 2 days brought little change by TLC. The reaction mixture was cooled, diluted with ethyl acetate, extracted with 10% HCl, dried over sodium sulfate, filtered, adsorbed onto silica, and purified by flash column using 10-30% ethyl acetate/hexanes to obtain 101 as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with 10% HCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. custompurified by flash column

Sources & evidence

ORD record
ord-4940e1b11b584d80bcfe021b7b274ce5
Source dataset
uspto-grants-2008_10
Patent number
US07432292B2

Reaction notes

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