Triethylamine → 2-Chloro-5-(2-phenoxyethoxycarbonyl)-4-trifluoromethyl-thiazole

HRID 846057Notes

Reaction equation

HRID 846057 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:11][C:12]1[S:13][C:14]([C:21](Cl)=[O:22])=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:11][C:12]1[S:13][C:14]([C:21]([O:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:22])=[C:15]([C:17]([F:18])([F:19])[F:20])[N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31236PhenoxyethanolHCID 132827442-Chloro-4-trifluoromethyl-5-thiazolecarbonyl chloride

Product 1

HCID 198845482-Chloro-5-(2-phenoxyethoxycarbonyl)-4-trifluoromethyl-thiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.3 g (0.045 mol) of 2-phenoxyethanol are added slowly while stirring to a solution of 11 g (0.44 mol) of 2-chloro-5-chlorcarbonyl-4-trifluoromethyl-thiazole in 100 ml of absolute toluene. The solution is then cooled to 0°-5° and 3.6 g (0.045 mol) of triethylamine are added dropwise while stirring. Triethylamine-hydrochloride precipitates from the reaction mixture. After everything is added, the suspension is stirred for 20 hours at room temperature and then poured onto ice-water. The organic phase is separated, dried over sodium sulfate and concentrated in a rotatory evaporator. The residue cristallizes. In order to purify it, the crystals are suspended in petrol-ether, filtered and dried. In this manner 8.7 g (57% of the theoreticl yield) of the title compound are obtained, m.p. 70°-72°.

Workup

  1. temperatureThe solution is then cooled to 0°-5°
  2. customTriethylamine-hydrochloride precipitates from the reaction mixture
  3. additionAfter everything is added
  4. stirringthe suspension is stirred for 20 hours at room temperature
  5. additionpoured onto ice-water
  6. customThe organic phase is separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in a rotatory evaporator
  9. customIn order to purify it
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-56d4af159b8b497a9c1b75c6da5672df
Source dataset
uspto-grants-1992_08
Patent number
US05135927

Reaction notes

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