Isopropanol → Isopropyl 2-Chloro-4-Trifluoromethyl-5-Thiazolecarboxylate

HRID 1413642Notes

Reaction equation

HRID 1413642 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:11](Cl)=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[CH:14]([OH:17])([CH3:16])[CH3:15]>>[Cl:1][C:2]1[S:3][C:4]([C:11]([O:17][CH:14]([CH3:16])[CH3:15])=[O:12])=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1

Participants

3

Reactant 2

HCID 3776IsopropanolHCID 132827442-Chloro-4-trifluoromethyl-5-thiazolecarbonyl chloride

Product 1

HCID 13282745Isopropyl 2-Chloro-4-Trifluoromethyl-5-ThiazolecarboxylateYield 86.1%

Procedure

The acid chloride of Example 8 (5.2 g), and 10 g of isopropanol were held at reflux for 16 hours. Excess alcohol was removed under reduced pressure. The residue was dissolved in 50 ml. of ether. The ether solution was washed with sodium bicarbonate, dried (MgSO4) and concentrated under reduced pressure. The crude product was distilled at 1 mm. on a Kugelrohr to give 4.9 g (86%) of the desired product as colorless liquid, nD25 =1.4655.

Workup

  1. temperatureat reflux for 16 hours
  2. customExcess alcohol was removed under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml
  4. washThe ether solution was washed with sodium bicarbonate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. distillationThe crude product was distilled at 1 mm

Sources & evidence

ORD record
ord-dde1fca615f14bff9fcb389d41a2bd89
Source dataset
uspto-grants-1981_02
Patent number
US04251261

Reaction notes

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