Hydrochloric Acid → Ethyl 5-[[2-(phenylsulfonyl)ethyl]thio]-4-thiazolecarboxylate

HRID 378518Notes

Reaction equation

HRID 378518 reaction equation
CC(C)([O-])C.[K+].[N+:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[C-:8].[C:15]1([S:21]([CH2:24][CH2:25]I)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.[C:28](=[S:30])=[S:29]>C1COCC1.C(OCC)(=O)C.O>[CH2:13]([O:12][C:10]([C:9]1[N:7]=[CH:8][S:29][C:28]=1[S:30][CH2:25][CH2:24][S:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:23])=[O:22])=[O:11])[CH3:14]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 533707Ethyl isocyanoacetateHCID 15885292(2-Iodoethanesulfonyl)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 15885293Ethyl 5-[[2-(phenylsulfonyl)ethyl]thio]-4-thiazolecarboxylateYield 56%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of potassium tert-butoxide (496 mg, 4.4 mmol) in 10 ml of THF was added a solution of ethyl isocyanoacetate (0.48 ml, 4.4 mmol) in 5 ml of THF at -40° C. and the reaction mixture was continued to stir for 10 min. After the reaction was cooled down to -60° C., a solution carbon disulfide in 5 ml of THF was added. The resulting mixture was allowed to warm up to 0° C. and 2-iodoethyl phenyl sulfone (4.4 mmol) was added. The mixture was then stirred at refluxed condition for 5 hours. After it was cooled down to room temperature, water and ethyl acetate were added. The aqueous layer was adjusted to acidic condition with dilute hydrochloric acid and extracted with ethyl acetate. The combined organic layer was dried with anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude residue was purified by chromatography to give the title compound (890 mg, 56%). 1H NMR (CDCl3) δ1.40 (t, 3H, J=7), 3.3-3.5 (m, 4H), 4.40 (q, 2H, J=7), 7.6 (t, 2H, J=8), 7.70 (t, 1H, J=8), 7.93 (d, 2H, J=8), and 8.64 (s, 1H).

Workup

  1. temperatureto warm up to 0° C.
  2. stirringThe mixture was then stirred
  3. temperatureat refluxed condition for 5 hours
  4. temperatureAfter it was cooled down to room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried with anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe crude residue was purified by chromatography

Sources & evidence

ORD record
ord-3d50c972c57c488b935427d65b03dd32
Source dataset
uspto-grants-2000_02
Patent number
US06030965

Reaction notes

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