Ethyl Acetate → 914452-60-1

HRID 1009980Notes

Reaction equation

HRID 1009980 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].CCOC(C)=O>C1COCC1.O.[Cl-].[Na+].O>[CH2:16]([O:15][C:13](=[O:14])[NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 775714-Bromobenzylamine

Product 1

HCID 25018359914452-60-1Yield 107.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-bromobenzylamine (5 g, 26.9 mmol) in THF (50 ml) and water (50 ml) was cooled down to 0° C. with sodium hydroxide (1.13 g, 28.2 mmol). Benzyl chloroformate (4.0 ml, 28.2 mmol) was added slowly and the reaction mixture was stirred at 0° C. for 1 h and at r.t. for 18 hours. Brine (50 ml) and EtOAc (50 mL) were added and the phases were separated. The aqueous phase was extracted with EtOAc (40 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness to yield a light pink solid (9.27 g, 100%). 1H NMR (300 MHz, CDCl3), δ: 4.34 (2 H, d, J=6.0 Hz, CH2NH), 5.14 (2 H, s, OCH2), 7.17 (2 H, d, J=8.1 Hz, Ar), 7.33-7.40 (5 H, m, Ar), 7.46 (2 H, d, J=8.3 Hz, Ar)

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with EtOAc (40 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-12873b7f7b9a41208151a2626fc12592
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

Loading…