Ethyl Acetate → HCID 67529065, compound

HRID 1867545Notes

Reaction equation

HRID 1867545 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[O:10]1[CH2:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].CN(C)C(N(C)C)=N.C(OCC)(=O)C>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:12]2[C:13](=[O:15])[CH2:14][O:10][C:11]2=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 664601,1,3,3-TetramethylguanidineHCID 685274-Bromobenzyl bromideHCID 973892,4-Oxazolidinedione

Product 1

HCID 67529065HCID 67529065, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.50 g (6 mmol) of 4-bromobenzyl bromide and 0.73 g (7.2 mmol) of 1,3-oxazolidine-2,4-dione in 6 ml of tetrahydrofuran is admixed dropwise with a solution of 1.39 g (12 mmol) of 1,1,3,3-tetramethylguanidine in 6 ml of tetrahydrofuran. The mixture is stirred at ambient temperature overnight. 50 ml of ice-cold aqueous hydrochloric acid (1N) and 100 ml of ethyl acetate are added. The organic phase is separated after settling out and washed successively with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution. It is dried over sodium sulphate and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on silica gel, eluting with an 80/20 mixture of cyclohexane and ethyl acetate. 1.14 g of product are obtained in the form of white crystals.

Workup

  1. customThe organic phase is separated
  2. washwashed successively with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution
  3. dry with materialIt is dried over sodium sulphate
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by chromatography on silica gel
  6. washeluting with an 80/20 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-f4dff77316564d93afc5ea399e47e5e4
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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