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

HRID 852352

반응식

HRID 852352 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-810db1beae524db89d963810bf7ccc3c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253192B2

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