Toluene → HCID 23134773, compound

HRID 2220151Notes

Reaction equation

HRID 2220151 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>O1CCOCC1>[CH2:8]([O:7][C:5]([C:4]1[CH:3]=[C:2]([NH:1][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=2)[CH:12]=[CH:11][CH:10]=1)=[O:6])[CH3:9]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11400Ethyl 3-aminobenzoateHCID 81531DiisopropylethylamineHCID 14916089Methyl 4-(bromomethyl)-α-oxobenzeneacetate

Product 1

HCID 23134773HCID 23134773, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-aminobenzoate (7.3 ml) and methyl 2-[4-(bromomethyl)phenyl]-2-oxoacetate (6.4 g) in dioxane (40 ml) was added diisopropylethylamine (6.4 ml), and the mixture was stirred at 60° C. for 2 hrs. The mixture was allowed to return to room temperature and toluene (330 ml) was added. The mixture was left standing at 0° C. for 5 hrs and the precipitated diisopropylethylamine hydrobromide was filtered off. The filtrate was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate and water. The ethyl acetate layer was separated, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate:4-1 v/v) to give the object compound (7.61 g) as a syrup.

Workup

  1. customto return to room temperature
  2. waitThe mixture was left
  3. waitstanding at 0° C. for 5 hrs
  4. filtrationthe precipitated diisopropylethylamine hydrobromide was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. customThe ethyl acetate layer was separated
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c4107cb7271420eafae2ff9ee63e833
Source dataset
uspto-grants-2008_08
Patent number
US07417052B2

Reaction notes

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