2,4-Dichlorophenol → Ethyl 2-(2',4'-dichlorophenoxy)-4-methyl-5-thiazolecarboxylate

HRID 2049943Notes

Reaction equation

HRID 2049943 reaction equation
Cl[C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[OH:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[O:21][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 594903Ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 13282762Ethyl 2-(2',4'-dichlorophenoxy)-4-methyl-5-thiazolecarboxylateYield 58.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.24 g (0.03 mole) of ethyl 2-chloro-4-methyl-5-thiazolecarboxylate, 4.89 g (0.03 mole) of 2,4-dichlorophenol, 4.14 g (0.03 mole) of potassium carbonate and 40 ml. of acetone was held at reflux for 89 hours. Acetone was removed under reduced pressure. The residue was treated with 50 ml. of water and extracted with ether. The ether solution was washed successively with saturated sodium bicarbonate, 30 ml. of 10% sodium hydroxide and 50 ml. of water. The ether solution was dried (MgSO4) and concentrated. The residue was recrystallized from hexane to give 5.8 g (58%) of ethyl 2-(2',4'-dichlorophenoxy)-4-methyl-5-thiazolecarboxylate as a white solid, m.p. 71°-73° C.

Workup

  1. temperatureat reflux for 89 hours
  2. customAcetone was removed under reduced pressure
  3. additionThe residue was treated with 50 ml
  4. extractionof water and extracted with ether
  5. washThe ether solution was washed successively with saturated sodium bicarbonate, 30 ml
  6. dry with materialThe ether solution was dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-0810748052c8476fb377897b7eb703ff
Source dataset
uspto-grants-1980_04
Patent number
US04199506

Reaction notes

Loading…