Boron trifluoride etherate → 3-Methoxy-10-nitro-6,11-dihydrodibenzo[b,e]thiepin-11-one

HRID 322237Notes

Reaction equation

HRID 322237 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:12]=2[C:13]([OH:15])=O)[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:13](=[O:15])[C:12]3[C:16]([N+:20]([O-:22])=[O:21])=[CH:17][CH:18]=[CH:19][C:11]=3[CH2:10][S:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 177896322-(3-Methoxyphenylthiomethyl)-6-nitrobenzoic acid

Product 1

HCID 220100313-Methoxy-10-nitro-6,11-dihydrodibenzo[b,e]thiepin-11-oneYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (30 ml) was suspended 2-(3-methoxyphenylthiomethyl)-6-nitrobenzoic acid obtained in Reference Example 17 (0.92 g, 2.88 mmol), and trifluoroacetic anhydride (0.81 ml, 5.76 mmol) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was ice-cooled, and boron trifluoride etherate (0.13 ml, 1.06 mmol) was added thereto, followed by reaction for one hour. After the reaction was completed, a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) to give 3-methoxy-10-nitro-6,11-dihydrodibenzo[b,e]thiepin-11-one (0.40 g, 46%).

Workup

  1. additionwas added
  2. temperaturecooled
  3. customfollowed by reaction for one hour
  4. washThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-d39967c57d644991a7898ca3d0ad90b0
Source dataset
uspto-grants-2001_04
Patent number
US06211227B1

Reaction notes

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