Boron trifluoride etherate → HCID 12794942, compound

HRID 867407Notes

Reaction equation

HRID 867407 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][C:10](=O)[C:4]=2[CH:3]=1.Cl.[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][SH:23].B(F)(F)F.CCOCC.[OH-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[C:10]([S:23][CH2:22][CH2:21][N:20]([CH3:24])[CH3:19])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherate2×HCID 14798Sodium HydroxideHCID 25798Captamine HydrochlorideHCID 12794939HCID 12794939, compound

Product 1

HCID 12794942HCID 12794942, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5.0 g of 10,11-dihydro-2-fluoro-11-oxodibenzo[b,f]thiepin in 52 ml of glacial acetic acid is added 5.81 g of β-dimethylaminoethanethiol hydrochloride. After the addition is complete, the mixture is heated to 90° C. whereupon it becomes homogenous. The solution is cooled to 25° C. and 15.4 ml of boron trifluoride etherate is added. After stirring for 3 days at 25° C., an additional 8 ml of boron trifluoride etherate is added and the solution is heated at 60° C. for 5 hours. The reaction mixture is poured into 150 ml of 20% sodium hydroxide solution at 0° C. The mixture is extracted with ether and the combined extracts are washed with 20% sodium hydroxide solution, water, saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Chromatography of the filtrate on silica gel with 5% methanol/dichloromethane elution provides 2-fluoro-11-[β-(dimethylamino)ethylthio]dibenzo[b,f]thiepin which is converted to its hydrochloride, mp 209°-211° C.

Workup

  1. additionAfter the addition
  2. temperatureThe solution is cooled to 25° C.
  3. temperaturethe solution is heated at 60° C. for 5 hours
  4. extractionThe mixture is extracted with ether
  5. washthe combined extracts are washed with 20% sodium hydroxide solution, water, saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. washChromatography of the filtrate on silica gel with 5% methanol/dichloromethane elution

Sources & evidence

ORD record
ord-1659233cf2a04e929bc86480b4243d19
Source dataset
uspto-grants-1988_10
Patent number
US04775672

Reaction notes

Loading…