Boron trifluoride etherate → HCID 1262426, compound

HRID 2424332Notes

Reaction equation

HRID 2424332 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[CH2:13]([SH:16])[CH2:14][SH:15].B(F)(F)F.CCOCC>CC(O)=O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[S:16][CH2:13][CH2:14][S:15]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 118405-Methylisatin

Product 1

HCID 1262426HCID 1262426, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

5-methyl-1H-indole-2,3-dione (6 g, 37 mmol) was suspended in 100 ml of AcOH. The heterogenous mixture was heated at 60° C. After complete solubilisation, 1,2-ethanedithiol (3.15 ml, 37 mmol) was added and then neat BF3.OEt2 (9.5 ml, 75 mmol) was added dropwise. The reaction was stirred for 25 minutes, in which time the reaction mixture became homogenous. After 20 minutes at room temperature, the reaction was quenched by addition of water, the solid washed several times with large amounts of water and air dried affording 5′-methylspiro[1,3-dithiolane-2,3′-indol]-2′(1′H)-one 6 as a brown solid.

Workup

  1. waitAfter 20 minutes at room temperature
  2. customthe reaction was quenched by addition of water
  3. washthe solid washed several times with large amounts of water and air
  4. customdried

Sources & evidence

ORD record
ord-4df138675c5a41cf826c6a88ac3c1673
Source dataset
uspto-grants-2011_06
Patent number
US07964593B2

Reaction notes

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