Hydrochloric Acid → HCID 19822191, compound

HRID 1030356Notes

Reaction equation

HRID 1030356 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:22])([CH3:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[O:11][C:10]([CH2:24][O:25][C:26]1[CH:39]=[CH:38][C:29]([CH2:30][CH:31]3[S:35][C:34](=N)[NH:33][C:32]3=[O:37])=[CH:28][CH:27]=1)([CH3:23])[CH2:9][C:8]2=[O:40])(=O)C.Cl.C[O:43]CCO>O>[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:21])([CH3:22])[CH2:16][C:17]([CH3:19])([CH3:18])[CH3:20])[O:11][C:10]([CH2:24][O:25][C:26]1[CH:39]=[CH:38][C:29]([CH2:30][CH:31]3[S:35][C:34](=[O:43])[NH:33][C:32]3=[O:37])=[CH:28][CH:27]=1)([CH3:23])[CH2:9][C:8]2=[O:40]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 140360584HCID 140360584, compound

Product 1

HCID 19822191HCID 19822191, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.2 g of 5-{4-[6-acetoxy-2-methyl-4-oxo-7-(1,1,3,3-tetramethylbutyl) chroman-2-ylmethoxy]-benzyl}-2-iminothiazolidin-4-one prepared as described in Preparation 26), 16 ml of 2N hydrochloric acid and 25 ml of ethylene glycol monomethyl ether was heated for 6 hours at 85°-90° C. under a nitrogen atmosphere. The reaction mixture was then poured into water and extracted with benzene. The benzene extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography, eluted with a 4:1 by volume mixture of benzene and ethyl acetate, to give the title compound as a slightly yellow foamy solid, softening at 100°-105° C.

Workup

  1. customprepared
  2. temperaturewas heated for 6 hours at 85°-90° C. under a nitrogen atmosphere
  3. extractionextracted with benzene
  4. extractionThe benzene extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. washeluted with a 4:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-b2322df6e4894c9387dc1ea6c24b05a0
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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