4-Ethylbenzoyl chloride → HCID 23628617, compound

HRID 1874094Notes

Reaction equation

HRID 1874094 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)[CH3:9]>C1COCC1>[CH2:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14](=[O:15])[S:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:12][CH:11]=1)[CH3:9]

Participants

4

Reactant 2

HCID 853684-Ethylbenzoyl chlorideHCID 178418616HCID 178418616, compound

Product 1

HCID 23628617HCID 23628617, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure,18 a solution of 2-mercaptopyridine (11.1 g, 100 mmol) in THF (100 mL) was treated with 4-ethylbenzoylchloride (16.9 g, 100 mmol). The resulting slurry was stirred for 30 min. The precipitate was collected by filtration and washed with hexanes (150 mL) in a Buchner funnel. The filtered material was added into a biphasic solution of saturated aqueous NaHCO3 (100 mL) and diethyl ether (100 mL). The mixture was stirred until the foaming subsided. The organic layer was removed and the water layer was extracted with diethyl ether. The combined organic extract was dried (Na2SO4), and filtered. The filtrate was concentrated to afford pale yellow solid. The solid was washed with hexanes (˜20 mL) to afford a pale yellow solid (20.9 g, 86%): mp 48-50° C.; 1H NMR δ 1.27 (t, J=7.6 Hz, 3H), 2.73 (q, J=7.6 Hz, 2H), 7.31-7.35 (m, 3H), 7.72-7.74 (m, 1H), 7.77-7.81 (m, 1H), 7.94-7.96 (m, 2H), 8.67-8.69 (m, 1H); 13C NMR δ 15.3, 29.1, 123.7, 127.9, 128.5, 131.0, 134.3, 137.3, 150.5, 151.2, 151.6, 189.0; FAB-MS obsd 244.0812, calcd 244.0796 [(M+H)+, M=C14H13NOS]. Anal. Calcd for C14H13NOS: C, 69.10; H, 5.39; N, 5.76. Found: C, 68.96; H, 5.38; N, 5.70.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with hexanes (150 mL) in a Buchner funnel
  3. additionThe filtered material was added into a biphasic solution of saturated aqueous NaHCO3 (100 mL) and diethyl ether (100 mL)
  4. stirringThe mixture was stirred until the foaming
  5. customThe organic layer was removed
  6. extractionthe water layer was extracted with diethyl ether
  7. extractionThe combined organic extract
  8. dry with materialwas dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customto afford pale yellow solid
  12. washThe solid was washed with hexanes (˜20 mL)

Sources & evidence

ORD record
ord-afff913d50b343bdb01ffb4e09cfe602
Source dataset
uspto-grants-2012_11
Patent number
US08304561B2

Reaction notes

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