Cesium carbonate → HCID 22313755, compound

HRID 584617Notes

Reaction equation

HRID 584617 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([NH:8][C:9]([NH2:11])=[O:10])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19]([CH:21]1[O:23][CH2:22]1)Br>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:19][CH:21]2[CH2:22][O:23]2)=[C:6]([NH:8][C:9]([NH2:11])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 18430EpibromohydrinHCID 11435385(5-Chloro-2-hydroxy-phenyl)-urea

Product 1

HCID 22313755HCID 22313755, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of N-(5-chloro-2-hydroxyphenyl)urea (53 mg, 0.28 mmol), cesium carbonate (92 mg, 0.28 mmol) and epibromohydrine (49 mg, 0.36 mmol) in dry DMF (0.6 mL) was stirred at room temperature for 24 hours. The mixture was then partitioned between ethyl acetate and water. The organic phase was washed with water three times, dried and concentrated to a solid residue. This crude product was recrystallized (ethyl ether and heptane to afford the subtitle compound (18 mg, 26.5%).

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water three times
  3. customdried
  4. concentrationconcentrated to a solid residue
  5. customThis crude product was recrystallized (ethyl ether and heptane

Sources & evidence

ORD record
ord-a68ee876c0814be99649b0abb316f120
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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