Iodine → HCID 67097044, compound

HRID 2078449Notes

Reaction equation

HRID 2078449 reaction equation
[CH:1]([O:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.[I:28]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[I:28][C:12]1[S:11][C:10]([O:9][C:8]2[CH:15]=[CH:16][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[N:14][CH:13]=1

Participants

8

Reactant 5

HCID 807IodineHCID 8058HexaneHCID 24477Sodium ThiosulfateHCID 670969222-(4-Isopropoxyphenoxy)-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 67097044HCID 67097044, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Example 7A (1.52 g, 6.5 mmole) in tetrahydrofuran (80 mL) at −78° C. was added a solution of 2.5M n-butyl lithium in hexane (2.84 mL, 7.1 mmole) and stirred for 2 hours. Solid iodine (1.80 g, 7.1 mmole) was added and the mixture was allowed to warm up to room temperature for an hour. The reaction mixture was diluted with ethyl acetate and added an aqueous solution of 10% sodium thiosulfate. The ethyl acetate layer was dried over magnesium sulfate, dried over magnesium sulfate and filtered through silica gel to remove polar impurities. The silica gel was washed with ethyl acetate until no UV active spot was apparent on TLC plate. Evaporation of the solvent yielded the title compound as light-yellow oil, 2.30 g (Quantitative). 1H NMR (300 MHz, CDCl3) δ ppm 7.29 (s, 1H) 7.09-7.22 (m, 2H) 6.84-6.96 (m, 2H) 4.42-4.61 (heptet, J=5.88 Hz, 1H) 1.34 (d, J=5.88 Hz, 6H). MS (ESI) m/z 362 (M+H)+.

Workup

  1. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered through silica gel
  4. customto remove polar impurities
  5. washThe silica gel was washed with ethyl acetate until no UV active spot
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1857acb917024f58b3612e034e74798e
Source dataset
uspto-grants-2011_04
Patent number
US07928243B2

Reaction notes

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