Hydrochloric Acid → HCID 15613928, compound

HRID 2351507Notes

Reaction equation

HRID 2351507 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:33]=[CH:32][C:12]([O:13][CH2:14][C:15]3([CH3:31])[CH2:24][C:23](=[O:25])[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:26]([O:28]CC)=[O:27])[CH:21]=4)[O:16]3)=[CH:11][CH:10]=2)[S:3]1.Cl>C(O)(=O)C>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:33]=[CH:32][C:12]([O:13][CH2:14][C:15]3([CH3:31])[CH2:24][C:23](=[O:25])[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:26]([OH:28])=[O:27])[CH:21]=4)[O:16]3)=[CH:11][CH:10]=2)[S:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15671167HCID 15671167, compound

Product 1

HCID 15613928HCID 15613928, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 530 mg of ethyl 2-[4-(2,4-dioxothiazolidin-5-ylmethyl) phenoxymethyl]-2-methyl-4-oxochroman-6-carboxylate (prepared as described in Example 14), 4 ml of acetic acid and 2 ml of 3N aqueous hydrochloric acid was heated under reflux for 5 hours. At the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure, and the residue was dissolved in diethyl ether. The resulting solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate; the solvent was then removed by evaporation under reduced pressure. The resulting residue was washed with warm water to afford 342 mg of the title compound as a pale yellow powder, softening at 105°-108° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customAt the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washThe resulting solution was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was then removed by evaporation under reduced pressure
  8. washThe resulting residue was washed with warm water

Sources & evidence

ORD record
ord-6a333d5a30d449068aaa1b21f1f6c6d5
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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