S,S-dimethylmethanesulfinyl iodide → HCID 86693323, compound

HRID 575293Notes

Reaction equation

HRID 575293 reaction equation
CS(I)(C)(C)=O.[CH3:7][C:8]([O-:11])([CH3:10])[CH3:9].[K+].[Br:13][C:14]1[CH:33]=[CH:32][C:17]2[O:18]CC(=O)C3[S:25][C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:23][C:22]=3[C:16]=2[CH:15]=1>ClCCl>[Br:13][C:14]1[CH:33]=[CH:32][C:17]2[O:18][CH2:7][C:8]3([C:10]4[S:25][C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:23][C:22]=4[C:16]=2[CH:15]=1)[CH2:9][O:11]3

Participants

5

Reactant 3

HCID 2723795S,S-dimethylmethanesulfinyl iodideHCID 23665647Potassium tert-butoxideHCID 86693324Ethyl 9-bromo-4-oxo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate

Product 1

HCID 86693323HCID 86693323, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of S,S-dimethylmethanesulfinyl iodide (1.15 g, 5.23 mmol, 1.60 equiv), t-BuOK (4 mL, 1.20 equiv) in dichloromethane (5 mL) at room temperature After 30 minutes a solution of ethyl 9-bromo-4-oxo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate (1.2 g, 3.26 mmol, 1.00 equiv) in dichloromethane (10 mL) was added slowly. The resulting solution was stirred for 5 h at room temperature, quenched with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:19) to give 600 mg (48%) of the titled compound as a off-white solid; LC-MS 382,384[M+H]+.

Workup

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customat room temperature
  4. customAfter 30 minutes
  5. additionwas added slowly
  6. customquenched with water
  7. extractionextracted with dichloromethane
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:19)

Sources & evidence

ORD record
ord-026c435b8af84c57b5123d4c49c51426
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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