Hydrochloric Acid → HCID 13768047, compound

HRID 1789360Notes

Reaction equation

HRID 1789360 reaction equation
[C:1]([N:4]=[C:5]([N:10]1[CH2:14][CH2:13][S:12][CH:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)[O:6]C(=O)C)(=[O:3])[CH3:2].C(O)C.[OH-].[Na+].Cl>O1CCCC1.O>[C:1]([NH:4][C:5]([N:10]1[CH2:14][CH2:13][S:12][CH:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:28][CH2:29]1)=[O:6])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 20188169HCID 20188169, compound

Product 1

HCID 13768047HCID 13768047, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.19 g of N,O-diacetyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboximidic acid, 20 ml of ethanol, 0.287 g of sodium hydroxide, 2.7 ml of water and 20 ml of tetrahydrofuran is stirred for 1.5 hours under ice-cooling. The mixture is neutralized with 10% hydrochloric acid, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=5:1). The eluate is concentrated under reduced pressure to remove solvent, and the residue is recrystallized from a mixture of ethyl acetate and n-hexane. 0.72 g of N-acetyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide is obtained.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto remove solvent
  7. customThe residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=5:1)
  8. concentrationThe eluate is concentrated under reduced pressure
  9. customto remove solvent
  10. customthe residue is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-aa76061cb7944db687e41e7774788579
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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