Acetic Acid → 2-{2-[2-(4-Phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789352Notes

Reaction equation

HRID 1789352 reaction equation
[N-:1]=[C:2]=[O:3].[Na+].[C:5]1([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH:26]3[NH:30][CH2:29][CH2:28][S:27]3)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[C:5]1([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH:26]3[N:30]([C:2]([NH2:1])=[O:3])[CH2:29][CH2:28][S:27]3)[CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 11051568NaNCOHCID 137680992-{2-[2-(4-Phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine

Product 1

HCID 137680362-{2-[2-(4-Phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamideYield 82.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 1.07 g of sodium isocyanate in 20 ml of water is added to a solution of 3.03 g of 2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine in 40 ml of ethanol, and 2.46 g of acetic acid are added thereto. The mixture is stirred at room temperature for 2 hours. 200 ml of water are added to the mixture, and the aqueous mixture is made alkaline with potassium carbonate. The aqueous mixture is extracted with ethyl acetate and chloroform, successively. The extracts are combined, washed with water, dried and then concentrated under reduced pressure to remove solvent. The residue is recrystallized from ethyl acetate. 2.78 g of 2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are obtained. Yield: 82.2%.

Workup

  1. additionare added
  2. extractionThe aqueous mixture is extracted with ethyl acetate and chloroform
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto remove solvent
  7. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-99a875cbc0914ffc94f639c96f95744e
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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