Cesium carbonate → HCID 68982994, compound

HRID 1820844Notes

Reaction equation

HRID 1820844 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:23].Br[CH2:25][C:26]#[N:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH2:25][C:26]#[N:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 68982158HCID 68982158, compound

Product 1

HCID 68982994HCID 68982994, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (351 mg, 0.918 mmol), prepared in step 1 of Example 3, bromoacetonitrile (77 μL, 1.11 mmol) and cesium carbonate (1.505 g, 4.62 mmol) in 25 mL of acetone was stirred under nitrogen at room temperature for 19 h (overnight). The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give {[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}acetonitrile (382 mg, 99%) as a light tan solid, mp 157-160° C. Elemental Analysis for C21H13BrN2OS Calc'd: C, 59.87; H, 3.11; N, 6.65. Found: C, 59.56; H, 3.28; N, 6.56.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove the acetone
  3. customThe residue was partitioned between methylene chloride and water
  4. customThe aqueous layer was separated
  5. extractionextracted three times with methylene chloride
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-dc59c67bc27d45b2abd55ffe91570872
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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