Triethylamine → 2-Isovalerylimino-3-(3-trifluoromethylphenyl)-5-ethylthiazoline

HRID 5311

Reaction equation

HRID 5311 reaction equation
[NH:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH:5]=[C:4]([CH2:17][CH3:18])[S:3]1.C(N(CC)CC)C.[C:26](Cl)(=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29]>C(Cl)(Cl)Cl>[C:26]([N:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=2)[CH:5]=[C:4]([CH2:17][CH3:18])[S:3]1)(=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66054Isovaleryl chlorideHCID 152396672-Imino-3-(3-trifluoromethylphenyl)-5-ethylthiazoline

Product 1

HCID 152396682-Isovalerylimino-3-(3-trifluoromethylphenyl)-5-ethylthiazolineYield 30.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-imino-3-(3-trifluoromethylphenyl)-5-ethylthiazoline (0.5 g) and triethylamine (0.6 g) in chloroform (30 ml), isovaleryl chloride (0.8 g) was dropwise added under stirring at room temperature, and stirring was continued for 2 hours. After removal of the solvent under reduced pressure, the concentrated residue was extracted with ethyl acetate (100 ml), washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.2 g of 2-isovalerylimino-3-(3-trifluoromethylphenyl)-5-ethylthiazoline (Compound No. 16).

Workup

  1. stirringstirring
  2. customAfter removal of the solvent under reduced pressure
  3. extractionthe concentrated residue was extracted with ethyl acetate (100 ml)
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0a08060894534fcf90c2c7601f6e0e43
Source dataset
uspto-grants-1993_09
Patent number
US05244863

Linked notes

Loading…