Hydrochloric Acid → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-ethyl-4-thiazolidinone

HRID 2941

Reaktionsgleichung

Reaktionsgleichung von HRID 2941
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][NH:19][C:18]2=[O:22])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[H-].[Na+].[CH2:25](I)[CH3:26].Cl>O1CCCC1.C(OCC)C.O>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][N:19]([CH2:25][CH3:26])[C:18]2=[O:22])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 1300035-(3,5-Bis(tert-butyl)-4-hydroxyphenyl)methylene-4-thiazolidinone

Produkt 1

HCID 537733605-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-ethyl-4-thiazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 9.58 g of 5-[[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]methylene]-4-thiazolidinone in 150 ml of tetrahydrofuran were added 1.20 g of a 60% dispersion of sodium hydride in mineral oil. After gas evolution ceased, 2.4 ml of ethyl iodide were added and the reaction mixture was stirred for two days under an argon atmosphere. The mixture was heated at reflux for six hours, cooled, diluted with diethyl ether and water, and adjusted to pH 3 with 1N hydrochloric acid. The layers were separated, and the organic layer was washed with a saturated sodium bicarbonate solution followed by a saturated sodium chloride solution. Concentration of the dried organic solution and chromatography of the resulting residue over silica gel eluting with a 10-30% ethyl acetate in hexane gradient provided 3.65 g of the desired title product, m.p. 169°-172.5° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for six hours
  3. temperaturecooled
  4. customThe layers were separated
  5. washthe organic layer was washed with a saturated sodium bicarbonate solution

Quellen und Nachweise

ORD-Eintrag
ord-99da04be27454cd9bffd7d2ff5f26253
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731336

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