Sulfuryl chloride → 4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1173042Notes

Reaction equation

HRID 1173042 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH:2]([CH3:4])[CH3:3].S(Cl)(Cl)(=O)=O.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22]([C:25](=[S:27])[NH2:26])=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[CH3:3][CH:2]([C:1]1[N:26]=[C:25]([C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:28])([F:17])[F:29])=[CH:24][CH:23]=2)[S:27][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:4]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 81583Ethyl isobutyrylacetateHCID 27348234-(Trifluoromethyl)thiobenzamide

Product 1

HCID 587658244-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 41.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl isobutyrylacetate (XI-3a) (3.006 g, 19.0 mmol) was dissolved in chloroform (20 mL). Sulfuryl chloride (1.70 mL, 21.2 mmol) was added and the solution was stirred at RT for 18 hours, then was concentrated. The residue was dissolved in ethanol (50 mL). 4-(Trifluoromethyl)benzenethioamide (4.234 g, 20.6 mmol) was added and the solution was heated to reflux for 24 hours. The mixture was cooled to RT and filtered. The solid was washed with cold ethanol and dried to provide the title product (2.68 g, 32%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.09 (d, J=8.1 Hz, 2H), 7.69 (d, J=8.1 Hz, 2H), 4.35 (q, J=7.1 Hz, 2H), 3.99 (qu, J=6.8 Hz, 1H), 1.39 (t, J=7.1 Hz, 3H), 1.35 (d, J=6.8 Hz, 6H).

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in ethanol (50 mL)
  3. temperaturethe solution was heated
  4. temperatureto reflux for 24 hours
  5. temperatureThe mixture was cooled to RT
  6. filtrationfiltered
  7. washThe solid was washed with cold ethanol
  8. customdried

Sources & evidence

ORD record
ord-0a96f727ebce4468a4808a8059582c70
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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