Water → HCID 68299382, compound

HRID 532476Notes

Reaction equation

HRID 532476 reaction equation
IC1C=C[C:5]([S:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.C(N([CH2:16][CH3:17])CC)C.[I:18][CH2:19][CH2:20][CH3:21].O.[CH3:23]N(C)C=O>>[I:18][C:19]1([S:8]([CH2:5][CH2:4][CH3:3])(=[O:10])=[O:9])[CH:17]=[CH:16][CH:23]=[CH:21][CH2:20]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 336431-IodopropaneHCID 11150443HCID 11150443, compound

Product 1

HCID 68299382HCID 68299382, compound

Procedure

4-iodo-benzenesulfinic acid (250 mg, 0.933 mmol) obtained in Step 20-1 was dissolved in dimethylformamide (3 mL), and triethylamine (0.2 mL, 1.21 mmol) and 1-iodopropane (0.3 mL, 2.33 mmol) was sequentially added thereto, followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction mixture was mixed with water and extracted three times with ethyl acetate, and the organic layer thus obtained was sequentially washed with water and a saline solution. The washed organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, followed by purification using column chromatography (Hex:EA=5:1) to obtain the title compound (200 mg).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted three times with ethyl acetate
  3. customthe organic layer thus obtained
  4. washwas sequentially washed with water
  5. dry with materialThe washed organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customfollowed by purification

Sources & evidence

ORD record
ord-161087276f4549c0b489607d939eeda4
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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