Boron tribromide → {2-[3-Ethyl-3-(3-hydroxy-phenyl)-2-oxo-azepan-1-yl]-ethyl}-urea

HRID 1594910Notes

Reaction equation

HRID 1594910 reaction equation
[CH2:1]([C:3]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:10][CH2:11][NH:12][C:13]([NH2:15])=[O:14])[C:4]1=[O:16])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:10][CH2:11][NH:12][C:13]([NH2:15])=[O:14])[C:4]1=[O:16])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21706296HCID 21706296, compound

Product 1

HCID 21706284{2-[3-Ethyl-3-(3-hydroxy-phenyl)-2-oxo-azepan-1-yl]-ethyl}-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of {2-[3-ethyl-3-(3-methoxy-phenyl)-2-oxo-azepan-1-yl]-ethyl}-urea (as described above in Step B) (0.14 g, 0.421 mmol) in CH2Cl2 (10 mL) at −78° C. was added BBr3 (1M, 0.842 mL, 0.842 rnmol). After stirring for 1 hr at 25° C. the reaction was quenched with H2O and partitioned with EtOAc and 10% HCl. The organic layer was washed with brine and dried (MgSO4), and the solvent removed in vacuo to obtain the title compound.

Workup

  1. customwas quenched with H2O
  2. custompartitioned with EtOAc and 10% HCl
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6ef19fefd0ef42df9ddbe26ae3a9b476
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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