Hydrochloric Acid → 4-(3-((2-(1-Hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)benzoic acid

HRID 28207

Reaktionsgleichung

Reaktionsgleichung von HRID 28207
[OH-].[Na+].[OH:3][C:4]1([CH2:10][CH2:11][N:12]2[C:16](=[O:17])[CH2:15][S:14][CH:13]2[CH2:18][CH2:19][CH2:20][C:21]2[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.CO.Cl>O>[OH:3][C:4]1([CH2:10][CH2:11][N:12]2[C:16](=[O:17])[CH2:15][S:14][CH:13]2[CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 12897184Ethyl 4-[3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl]benzoate

Produkt 1

HCID 1750274-(3-((2-(1-Hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Sodium hydroxide solution (5 N, 2.5 ml., 12.5 mmol.) is added to a stirred mixture of ethyl 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate (2.48 g., 5.91 mmol.), methanol (25 ml.) and water (5 ml.). The resulting mixture is stirred at ambient temperature for 16 l hours. Then, it is diluted with water, acidified with diluted hydrochloric acid, and extracted with ether. The ethereal extract is washed with water, dried over anhydrous magnesium sulfate, and filtered. Upon cooling the filtrate, the title compound precipitates out as a white solid, which is collected by filtration (7.06 g., 2.57 mmol., 42%). The product is recrystallized from chloroform-ether, m.p. 147°-148° C., ir (KBr) 3320, 1700, 1650 cm-1, pmr (CDCl3) δ3.54 (2H, s), 4.70 (1H, m), 7.22 (2H, d), 8.00 (2H, d).

Aufarbeitung

  1. extractionextracted with ether
  2. extractionThe ethereal extract
  3. washis washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. temperatureUpon cooling the filtrate
  7. customthe title compound precipitates out as a white solid, which
  8. filtrationis collected by filtration (7.06 g., 2.57 mmol., 42%)
  9. customThe product is recrystallized from chloroform-ether, m.p. 147°-148° C., ir (KBr) 3320, 1700, 1650 cm-1, pmr (CDCl3) δ3.54 (2H, s), 4.70 (1H, m), 7.22 (2H, d), 8.00 (2H, d)

Quellen und Nachweise

ORD-Eintrag
ord-11ca81f34b7c4d41aea0afe9d90a357a
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225609

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