Boron trifluoride etherate → HCID 12437468, compound

HRID 614190Notes

Reaction equation

HRID 614190 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([C:7]2[C:11]([C:12]([OH:14])=[O:13])=[CH:10][S:9][N:8]=2)=[CH:3][CH:2]=1.B(F)(F)F.[CH3:20][CH2:21]OCC>C(O)C>[C:1]1([CH3:15])[CH:2]=[CH:3][C:4]([C:7]2[C:11]([C:12]([O:14][CH2:20][CH3:21])=[O:13])=[CH:10][S:9][N:8]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 12437452HCID 12437452, compound

Product 1

HCID 12437468HCID 12437468, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(p-Tolyl)-4-isothiazolecarboxylic acid (1.5 g, 0.0068 mol), 20 ml of absolute ethanol, and boron trifluoride etherate (4.3 ml, 0.034 mol) were heated at reflux for 24 hours. Volatile materials were removed under reduced pressure. Water (25 ml) was added and the material extracted four times with ether. The ether was back-extracted with 5% NaHCO3, dried (CaSO4) and concentrated under reduced pressure to yield 1.51 g (0.0061 mol, 89.9%) of oil, nD25 = 1.5671.

Workup

  1. temperatureat reflux for 24 hours
  2. customVolatile materials were removed under reduced pressure
  3. additionWater (25 ml) was added
  4. extractionthe material extracted four times with ether
  5. extractionThe ether was back-extracted with 5% NaHCO3
  6. dry with materialdried (CaSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94669aa7e2414b3d92c8c20ca60e2e0c
Source dataset
uspto-grants-1979_03
Patent number
US04144047

Reaction notes

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