Triethylamine → HCID 86695309, compound

HRID 573512Notes

Reaction equation

HRID 573512 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:5][NH:6][C:7](=[O:15])OC1C=CC=CC=1.[C:20]([NH2:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21].C(N(CC)CC)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:5][NH:6][C:7]([NH:29][C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68509CumylamineHCID 86695310HCID 86695310, compound

Product 1

HCID 86695309HCID 86695309, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.00 g of phenyl 3-bromo-5-chlorophenoxycarbamate was dissolved in 50 ml of tetrahydrofuran. The resulting solution was added to a mixture of 1.54 g of cumylamine and 1.15 g of triethylamine, followed by stirring for 5 hours, while being heated to reflux. The reaction solvent was then distilled off under reduced pressure. The resulting residue was partially purified by silica gel column chromatography (eluent: hexane:ethyl acetate=3:1). The resulting crude crystal was washed with hexane to obtain 1-(3-Bromo-5-chlorophenoxy)-3-(2-phenylpropan-2-yl)urea (2.89 g, yield: 86%).

Workup

  1. temperaturewhile being heated to reflux
  2. distillationThe reaction solvent was then distilled off under reduced pressure
  3. customThe resulting residue was partially purified by silica gel column chromatography (eluent: hexane:ethyl acetate=3:1)
  4. washThe resulting crude crystal was washed with hexane

Sources & evidence

ORD record
ord-8488cd6f45504f09baea39a88b0cd8cd
Source dataset
uspto-grants-2015_05
Patent number
US09029601B2

Reaction notes

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