1,2-Dichloroethane → Diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylate

HRID 23591Notes

Reaction equation

HRID 23591 reaction equation
[C:1]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=[C:5]([C:7]([O-:9])=O)[CH:4]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=1.Cl.[CH2:21]([O:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN1CCOCC1.C(Cl)CCl>>[C:22]1([CH2:21][O:28][NH:29][C:7]([C:5]2[CH:4]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=[C:1]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=2)=[O:9])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 102312Benzyloxyamine hydrochlorideHCID 225750493,5-Bis(ethoxycarbonyl)benzoate

Product 1

HCID 12017544Diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylateYield 59%

Procedure

To a solution of diethyl 1,3,5-benzenetricarboxylate (3.192 g, 20 mol) and O-benzylhydroxyamine hydrochloride (4.789 g, 19 mmol) in 40 mL were added N-methylmorpholine (2.2 mL, 20 mmol) and EDC (3.834 g, 20 mmol) at 0° C., and the mixture was stirred at room temperature for 20 hours. The solvent was removed by evaporator and the residue was dissolved in EtOAc (150 mL). The organic solution was washed with 1 N HCL (150 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over Na2SO4, and concentrated to give white solid. This material was recrystallized from EtOAc to give 4.154 g of white powder (59% yield).

Workup

  1. customThe solvent was removed by evaporator
  2. dissolutionthe residue was dissolved in EtOAc (150 mL)
  3. washThe organic solution was washed with 1 N HCL (150 mL)
  4. washwashed with saturated aqueous NaHCO3 (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give white solid
  8. customThis material was recrystallized from EtOAc

Sources & evidence

ORD record
ord-960ef9b7f6a741cfb55e760cfcb8604c
Source dataset
uspto-grants-2005_02
Patent number
US06852750B2

Reaction notes

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