Hydrochloric Acid → 4,4'-Disulfanediylbis(2-methylphenol)

HRID 852352

Reaktionsgleichung

Reaktionsgleichung von HRID 852352
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([S:10]C#N)[CH:7]=[CH:6][C:5]=1[OH:13].[CH3:14][C:15]1[CH:16]=[C:17]([S:26]CC2SC(C3C=CC(C(F)(F)F)=CC=3)=NC=2C)[CH:18]=[CH:19][C:20]=1[O:21]CC(O)=O.Cl>O.CCOCC>[C:15]1([CH3:14])[C:20]([OH:21])=[CH:19][CH:18]=[C:17]([S:26][S:10][C:8]2[CH:9]=[C:4]([CH3:3])[C:5]([OH:13])=[CH:6][CH:7]=2)[CH:16]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 220928((4-Hydroxy-3-methylphenyl)sulfanyl)formonitrileHCID 9803963GW 501516

Produkt 1

HCID 115364374,4'-Disulfanediylbis(2-methylphenol)

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a stirred solution of 33.0 g (825.6 mmol) NaOH in 200 ml water was added 44.0 g (266.3 mmol) of 2-methyl-4-thiocyanato-phenol at 85° C. [Wei, Zhi-Liang; Kozikowski, Alan P., A Short and Efficient Synthesis of the Pharmacological Research Tool GW501516 for the Peroxisome Proliferator-Activated Receptor delta, Journal of Organic Chemistry (2003), 68(23), 9116-9118]. The temperature was raised to 95° C. and the mixture stirred over night. After cooling (10° C.), ether and 90 ml of aqueous conc. HCl were added. The water phase was extracted with ether (two times). The organic phase was washed with brine, dried (Na2SO4) and evaporated. The residue was dissolved in 300 ml of DMSO and heated for 2 h at 95° C. Subsequently, the solution was poured onto ice water and extracted with three 1 l portions of TBME. The organic layers were washed with 700 ml of water, dried (Na2SO4) and evaporated to give 42.1 g of the title compound.

Aufarbeitung

  1. additionwere added
  2. extractionThe water phase was extracted with ether (two times)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in 300 ml of DMSO
  7. temperatureheated for 2 h at 95° C
  8. additionSubsequently, the solution was poured onto ice water
  9. extractionextracted with three 1 l portions of TBME
  10. washThe organic layers were washed with 700 ml of water
  11. dry with materialdried (Na2SO4)
  12. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-810db1beae524db89d963810bf7ccc3c
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253192B2

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