Sodium Iodide → HCID 490090, compound

HRID 1197861Notes

Reaction equation

HRID 1197861 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11]Cl)=[CH:5][CH:6]=1.[I-].[Na+].[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:24][CH2:25][CH2:26][N:27]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[S:3][C:4]([C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[O:24][CH2:25][CH2:26][N:27]=3)=[CH:21][CH:22]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1012874-(4,5-Dihydro-1,3-oxazol-2-yl)phenolHCID 103992482-Chloro-5-(5-chloropentanoyl)thiophene

Product 1

HCID 490090HCID 490090, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture consisting of 2-chloro-5-(5-chloropentanoyl)thiophene (3c) (2.13 g, 0.009 mol), sodium iodide (1.1 g, 0.0073 mol), 2-(4-hydroxyphenyl)-4,5-dihydro-oxazole (1.99 g, 0.010 mol), and anhydrous potassium carbonate (5.2 g, 0.045 mol) in acetonitrile (50 ml) was refluxed for 48 hrs., cooled and filtered. The resulting solution was deprived of the solvent and the residue was taken up with ethyl acetate (100 ml). After washing with water and subsequent drying on anydrous sodium sulfate the solution was evaporated to dryness. The resulting solid was crystallized via benzene:cyclohexane (1:1) to give pure 4c (3.17 g; 97%). M.p. 143°-144° C. Anal. (C18H18ClNO3S).

Workup

  1. temperaturewas refluxed for 48 hrs
  2. temperature, cooled
  3. filtrationfiltered
  4. washAfter washing with water
  5. dry with materialsubsequent drying on anydrous sodium sulfate the solution
  6. customwas evaporated to dryness
  7. customThe resulting solid was crystallized via benzene:cyclohexane (1:1)

Sources & evidence

ORD record
ord-a13de92e1d1b4789889637993b7a0572
Source dataset
uspto-grants-1994_01
Patent number
US05278184

Reaction notes

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