Cesium carbonate → HCID 22313676, compound

HRID 965901Notes

Reaction equation

HRID 965901 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Br.[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([NH2:16])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[O:5]1[CH2:4][CH:3]1[CH2:1][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([NH2:16])=[O:15]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 18430EpibromohydrinHCID 70964(2-Hydroxyphenyl)urea

Product 1

HCID 22313676HCID 22313676, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of epibromohydrin (0.94 g, 6.84 mmol) in dry DMF (2 mL) was added dropwise to a stirred suspension of N-(2-hydroxyphenyl)urea (0.65 g, 4.27 mmol) and cesium carbonate (2.22 g, 6.84 mmol) in DMF (8 mL). After 2 hours the mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with water (3 times), dried and concentrated. The semi-solid residue was disssolved in dichloromethane/ethyl ether, filtered and heptane was added to turbidity. After standing at room temperature overnight, the solid was filtered to afford the subtitle compound (0.28 g, 32%).

Workup

  1. customAfter 2 hours the mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic phase was washed with water (3 times)
  4. customdried
  5. concentrationconcentrated
  6. filtrationfiltered
  7. additionheptane was added to turbidity
  8. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-8a009b18638b45e6a83b8cbb64d599af
Source dataset
uspto-grants-2005_10
Patent number
US06951874B2

Reaction notes

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