Ethanol → HCID 13282764, compound

HRID 1903670Notes

Reaction equation

HRID 1903670 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].Cl[C:6]1[S:7][C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([C:11](F)(F)F)[N:10]=1.[CH2:20]([OH:22])[CH3:21]>>[CH2:2]([O:1][C:6]1[S:7][C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([C:11]([O:17][CH2:18][CH3:19])([O:16][CH2:15][CH3:8])[O:22][CH2:20][CH3:21])[N:10]=1)[CH3:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 13282764HCID 13282764, compound

Procedure

To a warm solution of sodium ethoxide prepared from 2.0 g (0.0869 mole) of Na and 50 ml. of ethanol was added 5.2 g (0.02 mole) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate. The mixture was stirred for 4 hours. Ethanol was removed under reduced pressure. The residue was treated with water and extracted with ether. The ether solution was washed with saturated sodium bicarbonate, dried (MgSO4) and concentrated under reduced pressure. The residue was distilled to give 2.2 g of the desired product as an oil, b.p. 115° C. at 0.1 mm; nD25 =1.4776.

Workup

  1. customEthanol was removed under reduced pressure
  2. additionThe residue was treated with water
  3. extractionextracted with ether
  4. washThe ether solution was washed with saturated sodium bicarbonate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-e5d74d72915942a6945c5b50180b222c
Source dataset
uspto-grants-1984_03
Patent number
US04437875

Reaction notes

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