Urea → HCID 135589888, compound

HRID 422066Notes

Reaction equation

HRID 422066 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH3:20])[CH:14]=1)=O.[NH2:21][C:22]([NH2:24])=[O:23]>Cl.O1CCOCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[NH:24][C:22](=[O:23])[N:21]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH3:20])[CH:14]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 66673011HCID 66673011, compound

Product 1

HCID 135589888HCID 135589888, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (E)-3-(2,3-dichlorophenyl)-1-(4-hydroxy-3-methylphenyl)prop-2-en-1-one (123 mg, 0.4 mmol) and urea (28 mg, 2.0 mmol,) (SIGMA-ALDRICH) in 4N HCl/dioxane (5 mL) was heated to 120° C. in a sealed vessel overnight. The reaction was complete as determined by LCMS, and the solution was cooled to room temperature. The crude reaction mixture was purified by reverse-phase HPLC (acetonitrile/10 mM aqueous ammonium acetate) to yield the desired product (35 mg, 25%) 1H NMR (400 MHz, d6-DMSO): 7.93 (s, 1H), 7.80-7.82 (dd, 1H), 7.49-7.58 (m, 2H), 7.09 (s, 1H), 6.88 (d, 1H), 2.18 (s, 3H). MS (EI) for C17H12Cl2N2O2: 348.5 (MH+).

Workup

  1. temperaturethe solution was cooled to room temperature
  2. customThe crude reaction mixture
  3. customwas purified by reverse-phase HPLC (acetonitrile/10 mM aqueous ammonium acetate)

Sources & evidence

ORD record
ord-dc95805fd0ab4d6aa7f2811ba06dc1db
Source dataset
uspto-grants-2012_01
Patent number
US08101625B2

Reaction notes

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