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

HRID 443669Notes

Reaction equation

HRID 443669 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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 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) δ 3.54 (2H, s), 4.70 (1H, m), 7.22 (2H, d), 8.00 (2H, d).

Workup

  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) δ 3.54 (2H, s), 4.70 (1H, m), 7.22 (2H, d), 8.00 (2H, d)

Sources & evidence

ORD record
ord-db9dc6039da24b50870b944469a6e3dd
Source dataset
uspto-grants-1981_04
Patent number
US04260771

Reaction notes

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