Potassium Carbonate → HCID 13519360, compound

HRID 1253119Notes

Reaction equation

HRID 1253119 reaction equation
[OH:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]([CH3:23])[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:33]1[S:34][C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=1>CN(C)C=O>[S:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=[C:33]1[O:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]([CH3:23])[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]2[C:16]([Cl:22])=[CH:17][CH:18]=[CH:19][C:20]=2[Cl:21])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119872-ChlorobenzothiazoleHCID 13884580HCID 13884580, compound

Product 1

HCID 13519360HCID 13519360, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

38.5 g of 2-(2,6-dichlorobenzyloxy)ethyl 2-(4-hydroxyphenoxy)-propionate were dissolved in 200 ml of dimethylformamide and 15.2 g of potassium carbonate were added to the solution. The mixture was stirred at 80° C. for 1 hour. A solution of 18.6 g of 2-chlorobenzothiazole in 50 ml of dimethylformamide was added dropwise at this temperature to the resulting mixture. After the addition, the mixture was stirred at the same temperature for 2 hours to complete the reaction. The reaction mixture was poured onto ice water, and the separated oily product was extracted with toluene. The toluene layer was washed successively with a 1% aqueous solution of sodium hydroxide and water, and then toluene was evaporated under reduced pressure to give 43.5 g of 2-(2,6-dichlorobenzyloxy)ethyl 2-[4-(benzothiazol-2-yloxy)phenoxy]propionate as a viscous oily product represented by the formula above.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at the same temperature for 2 hours
  3. customthe reaction
  4. additionThe reaction mixture was poured onto ice water
  5. extractionthe separated oily product was extracted with toluene
  6. washThe toluene layer was washed successively with a 1% aqueous solution of sodium hydroxide and water
  7. customtoluene was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3ba631fbd8744661b6e3ada84a45f1ae
Source dataset
uspto-grants-1988_05
Patent number
US04747865

Reaction notes

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