Iodine → HCID 68494041, compound

HRID 2381788Notes

Reaction equation

HRID 2381788 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:11]([NH:18][C:19]([C:21]1[S:25][CH:24]=[N:23][C:22]=1[CH3:26])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I:27]I>O1CCCC1>[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([I:27])=[N:23][C:22]=1[CH3:26])=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 807IodineHCID 2733832Lithium HexamethyldisilazideHCID 45823040HCID 45823040, compound

Product 1

HCID 68494041HCID 68494041, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of lithium hexamethyldisilazide (4.63 g, 27.65 mmol) in anhydrous tetrahydrofuran (25 mL) was added dropwise to a solution of N-benzyl-4-methylthiazole-5-carboxamide (2.79 g, 12.02 mmol) in anhydrous tetrahydrofuran (25 mL) at −78° C. under nitrogen atmosphere. The reaction mixture was stirred at −78° C. for 1 hour, then iodine (1.68 g, 13.22 mmol) was added in portions. The mixture was stirred at ambient temperature for 90 minutes, quenched with methanol (2 mL) and water (2 mL). The solvent was removed in vacuo and the residue was diluted with water (30 mL) and extracted with dichloromethane (3×40 mL). The organic layers were combined, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography (20-35% ethyl acetate in hexanes) to afford the title compound as a white solid (2.03 g, 47%): 1H NMR (300 MHz, CDCl3) δ 7.39-7.30 (m, 5H), 6.02 (br s, 1H), 4.57 (d, J=6.0 Hz, 2H), 2.68 (s, 3H); MS (ES+) m/z 359.1 (M+1).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 90 minutes
  2. customquenched with methanol (2 mL) and water (2 mL)
  3. customThe solvent was removed in vacuo
  4. additionthe residue was diluted with water (30 mL)
  5. extractionextracted with dichloromethane (3×40 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (20-35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-48d5dc46a7e8446199d8c7cc4900d598
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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