Sodium Hydroxide → 4-{3-[3-[2-(1-Cyclohexenyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

HRID 28208Notes

Reaction equation

HRID 28208 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[C:13](=[O:14])[CH2:12][S:11][CH:10]2[CH2:15][CH2:16][CH2:17][C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[OH-].[Na+]>CO.O>[C:1]1([CH2:7][CH2:8][N:9]2[C:13](=[O:14])[CH2:12][S:11][CH:10]2[CH2:15][CH2:16][CH2:17][C:18]2[CH:28]=[CH:27][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23339590Ethyl 4-{3-[3-[2-(1-cyclohexenyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate

Product 1

HCID 233395764-{3-[3-[2-(1-Cyclohexenyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 4-{3-[3-[2-(1-cyclohexenyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoate (Example 4, Step B) (4.0 g., 0.01 mole) and sodium hydroxide (1.2 g., 0.003 mole) in methanol (50 ml.) and water (5 ml.) is allowed to stand at 25° C. for 18 hours. The methanol is distilled at reduced pressure. The residual solution is treated with water (50 ml.) and acidified with 2 N hydrochloric acid. The title compound precipitates as an oil that gradually crystallizes. It is collected, washed with water, and air dried.

Workup

  1. distillationThe methanol is distilled at reduced pressure
  2. additionThe residual solution is treated with water (50 ml.)
  3. customThe title compound precipitates as an oil that
  4. customgradually crystallizes
  5. customIt is collected
  6. washwashed with water, and air
  7. customdried

Sources & evidence

ORD record
ord-71c608246ba14c09861741830384aae6
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Reaction notes

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