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

HRID 2049934Notes

Reaction equation

HRID 2049934 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 16 (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-583b7ab5798d4539847396c5f03105d9
Source dataset
uspto-grants-1980_04
Patent number
US04199506

Reaction notes

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