Boron Trichloride → HCID 66816495, compound

HRID 1754978Notes

Reaction equation

HRID 1754978 reaction equation
B(Cl)(Cl)Cl.C([O:12][CH2:13][CH2:14][N:15]([C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Br:29])=[C:24]([CH3:30])[CH:23]=1)[C:16]([NH:18][CH2:19][CH2:20][OH:21])=[O:17])C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:29][C:25]1[C:24]([CH3:30])=[CH:23][C:22]([N:15]([CH2:14][CH2:13][OH:12])[C:16]([NH:18][CH2:19][CH2:20][OH:21])=[O:17])=[CH:27][C:26]=1[CH3:28]

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 66816899HCID 66816899, compound

Product 1

HCID 66816495HCID 66816495, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride (0.93 ml, 0.93 mmol, 1.0 M solution in dichloromethane) was added to a solution of 1-(2-(benzyloxy)ethyl)-1-(4-bromo-3,5-dimethylphenyl)-3-(2-hydroxyethyl)urea (98 mg, 0.23 mmol) in anhydrous dichloromethane (4.6 ml) at −78° C., and the mixture was stirred at the same temperature for two hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic phase was sequentially washed with water and saturated brine and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 1-(4-bromo-3,5-dimethylphenyl)-1,3-bis(2-hydroxyethyl)urea (64 mg, 83%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic phase was sequentially washed with water and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-21837ce94fa04eb9a1b39264d71737b2
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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