Potassium Carbonate → HCID 68907694, compound

HRID 1592810Notes

Reaction equation

HRID 1592810 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 181293-BromophenylureaHCID 27339602-Thiopheneboronic acid

Product 1

HCID 68907694HCID 68907694, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

3-Bromopheylurea (10.40 g), 2-thiopheneboronic acid (8.20 g) and palladium tetrakistriphenylphosphine (2.63 g) were added to a flask containing 300 mL of dimethoxyethane and 100 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 90° C. overnight. The reaction mixture was then cooled to room temperature and partitioned between EtOAc and water. The EtOAc layer was dried over MgSO4, filtered and concentrated under vacuum. The resulting residue was tritutrated with ethyl ether to give 9.00 g of 1-(3-(thiophen-2-yl)phenyl)urea.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. dry with materialThe EtOAc layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7a4a3044be9048229e636b0f325cb9c5
Source dataset
uspto-grants-2007_11
Patent number
US07294616B2

Reaction notes

Loading…