Boron trifluoride etherate → HCID 12437468, compound

HRID 1448691Notes

Reaction equation

HRID 1448691 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-3e730a6f80ca4f00a5571c1d2dc390ef
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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