Hydrochloric Acid → HCID 20245606, compound

HRID 1589689Notes

Reaction equation

HRID 1589689 reaction equation
C([O:4][C:5]1[C:6]([CH3:37])=[C:7]2[C:12](=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[O:11][C:10]([CH2:20][CH2:21][O:22][C:23]1[CH:36]=[CH:35][C:26]([CH2:27][CH:28]3[S:32][C:31](=N)[NH:30][C:29]3=[O:34])=[CH:25][CH:24]=1)([CH3:19])[CH2:9][CH2:8]2)(=O)C.Cl.[OH2:39]>COCCO>[OH:4][C:5]1[C:6]([CH3:37])=[C:7]2[C:12](=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[O:11][C:10]([CH2:20][CH2:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][CH:28]3[S:32][C:31](=[O:39])[NH:30][C:29]3=[O:34])=[CH:35][CH:36]=1)([CH3:19])[CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 140341593HCID 140341593, compound

Product 1

HCID 20245606HCID 20245606, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

560 mg of 5-{4-[2-(6-acetoxy-7,8-dimethoxy-2,5-dimethylchroman-2-yl)ethoxy]benzyl}-2-iminothiazolidin-4-one (prepared as described in Example 7) were added to a mixture of 7 ml of concentrated hydrochloric acid, 2.5 ml of water and 10 ml of ethylene glycol monomethyl ether, and the mixture was heated under reflux for 13 hours. The reaction mixture was then processed and purified as described in Example 1(a), except that the crude product, in the form of an oil, was purified by column chromatography through silica gel eluted with a 9:1 by volume mixture of chloroform and ethyl acetate, to give the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 13 hours
  3. custompurified
  4. customwas purified by column chromatography through silica gel
  5. washeluted with a 9:1 by volume mixture of chloroform and ethyl acetate

Sources & evidence

ORD record
ord-c54e2e9c2d954c589b05a8d56300e8e7
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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