Potassium Carbonate → HCID 13117186, compound

HRID 851279Notes

Reaction equation

HRID 851279 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([O:9][C:10]3[CH:21]=[CH:20][C:13]([O:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:31]1[CH2:36][CH2:35][O:34][C:32]1=[O:33]>CC(C)=O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([O:9][C:10]3[CH:21]=[CH:20][C:13]([O:14][CH:15]([CH3:19])[C:16]([O:18][CH:31]4[CH2:36][CH2:35][O:34][C:32]4=[O:33])=[O:17])=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 156003Fenthiaprop

Product 1

HCID 13117186HCID 13117186, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
45 °C

Procedure

21 g (0.06 mole) of 2-[4-(6-chloro-2-benzthiazolyloxy)-phenoxy]-propionic acid were initially taken together with 10.4 g (0.075 mole) of potassium carbonate in 100 ml of acetone and the mixture was stirred for approx. 1/2 hour at 45° C., a thick paste being formed. 11.6 g (0.07 mole) of 2-bromobutyrolactone in 50 ml of acetone were then added dropwise in the course of 1/2 hour. When the addition was complete, the reaction mixture became highly fluid; the conversion was followed by means of thin-layer chromatography and was approx. 70% after 5 hours. Altogether, the mixture was stirred for 16 hours at approx. 50° C. After cooling, the salt was filtered off, the acetone was removed by distillation and the residue was taken up in approx. 200 ml of toluene and washed with water and saturated sodium bicarbonate solution. After drying, the toluene was removed by distillation and the residue remaining was dried in vacuo (0.05 mbar) for one hour at approx. 70° C. The product remaining after drying was 22 g (91.3% of theory) of a very viscous oil, which was identified by 1H nuclear magnetic resonance spectroscopy as 2-oxotetrahydrofuran-3-yl 2-[4-(6-benzthiazolyloxy)-phenoxy]-propanoate. ##STR12##

Workup

  1. customa thick paste being formed
  2. additionWhen the addition
  3. customafter 5 hours
  4. stirringAltogether, the mixture was stirred for 16 hours at approx. 50° C
  5. temperatureAfter cooling
  6. filtrationthe salt was filtered off
  7. customthe acetone was removed by distillation
  8. washwashed with water and saturated sodium bicarbonate solution
  9. customAfter drying
  10. customthe toluene was removed by distillation
  11. customthe residue remaining was dried in vacuo (0.05 mbar) for one hour at approx. 70° C
  12. customafter drying

Sources & evidence

ORD record
ord-f519f35a163846bc90df2d142f4a8d03
Source dataset
uspto-grants-1983_05
Patent number
US04383850

Reaction notes

Loading…