Hydrochloric Acid → [3-Cyclohexyl-2-(cyclohexylimino)-4-oxo-5-thiazolidinylidene]acetic acid

HRID 867448Notes

Reaction equation

HRID 867448 reaction equation
[CH:1]1([N:7]2[C:11](=[O:12])[C:10](=[CH:13][C:14]([O:16]C)=[O:15])[S:9][C:8]2=[N:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[I-].[Li+].Cl>CN(C)C=O.O>[CH:1]1([N:7]2[C:11](=[O:12])[C:10](=[CH:13][C:14]([OH:16])=[O:15])[S:9][C:8]2=[N:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 3967510Methyl [3-cyclohexyl-2-(cyclohexylimino)-4-oxo-5-thiazolidinylidene]acetate

Product 1

HCID 54247385[3-Cyclohexyl-2-(cyclohexylimino)-4-oxo-5-thiazolidinylidene]acetic acidYield 67.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl [3-cyclohexyl-2-(cyclohexylimino)-4-oxo-5-thiazolidinylidene]acetate (5.0 g, 14 mmoles) and anhydrous lithium iodide (7.6 g, 57 mmoles) in N,N-dimethylformamide (30 mls) is heated under argon to reflux. After six hours the mixture is cooled, diluted with water, acidified with 4N HCl, and extracted twice with dichloromethane. The combined extracts are washed with brine and dried over MgSO4. The solvent is removed to afford a syrupy residue which evenually crystallizes. Recrystallization from acetonitrile gave the product (3.2 g), mp 189°-190° C.

Workup

  1. temperatureis heated under argon
  2. temperatureto reflux
  3. temperatureAfter six hours the mixture is cooled
  4. extractionextracted twice with dichloromethane
  5. washThe combined extracts are washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent is removed
  8. customto afford a syrupy residue which
  9. customevenually crystallizes
  10. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-62b0d1a1851d45a79744ced82a0f96dc
Source dataset
uspto-grants-1988_10
Patent number
US04775677

Reaction notes

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