Cesium carbonate → HCID 86601496, compound

HRID 270137Notes

Reaction equation

HRID 270137 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.[N+](C1C=C(S(O[CH2:26][C@@H:27]2[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:26][C@@H:27]2[CH2:29][O:28]2)=[C:6]([NH:8][C:9]([NH2:11])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 11435385(5-Chloro-2-hydroxy-phenyl)-urea

Product 1

HCID 86601496HCID 86601496, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(5-chloro-2-hydroxyphenyl)urea (0.9 g, 4.9 mmol) and (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.0 g, 3.8 mmol) in dimethylformamide were stirred under nitrogen. Cesium carbonate (1.9 g, 5.7 mmol) was added to the mixture and the reaction was stirred under nitrogen at room temperature over night. The mixture was partitioned between water and dichloromethane, and the organic phase was washed with water. After drying, filtration and evaporation of the solvent 0.48 g, (52%) of subtitle compound was obtained.

Workup

  1. customThe mixture was partitioned between water and dichloromethane
  2. washthe organic phase was washed with water
  3. customAfter drying
  4. filtrationfiltration and evaporation of the solvent 0.48 g, (52%) of subtitle compound
  5. customwas obtained

Sources & evidence

ORD record
ord-cab8484e240f41c09b9f2633461508bc
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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