Azobisisobutyronitrile → HCID 14820509, compound

HRID 1088729Notes

Reaction equation

HRID 1088729 reaction equation
[OH:1][C:2]1[C:3]([CH2:11][CH:12]=[CH2:13])=[CH:4][C:5]2[S:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.CC(N=NC(C#N)(C)C)(C#N)C.[C:26]1([SH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(=O)(O)[O-].[Na+]>[OH:1][C:2]1[C:3]([CH2:11][CH2:12][CH2:13][S:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:5]2[S:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7969ThiophenolHCID 14820507HCID 14820507, compound

Product 1

HCID 14820509HCID 14820509, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-hydroxy-6-allyl-2,3-dihydrobenzothiophene (125 mg, 0.65 mmole) in 0.5 mL thiophenol was added 28 mg AIBN. The reaction mixture was purged with nitrogen and heated to 90° C. for 3 hours. TLC analysis (90/10 hexane/EtOAc) showed the reaction to be complete. The reaction mixture was diluted with 25 mL saturated sodium bicarbonate and extracted 3×25 mL EtOAc. The combined organics were washed with sodium bicarbonate (2×25 mL), H2O (1×25 mL) and brine (1×25 mL). Drying over Na2SO4, filtration and concentration afforded 568 mg crude product as an oil. Purification by flash chromatography (90/10, hexane/EtOAc) 126 mg (64%) pure product NMR 287 MS181.

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. customthe reaction
  3. extractionextracted 3×25 mL EtOAc
  4. washThe combined organics were washed with sodium bicarbonate (2×25 mL), H2O (1×25 mL) and brine (1×25 mL)
  5. dry with materialDrying over Na2SO4, filtration and concentration

Sources & evidence

ORD record
ord-eb4b33dc41cf49bf8a81edf437f616f9
Source dataset
uspto-grants-1990_10
Patent number
US04963580

Reaction notes

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