Methyl Isocyanate → N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789350Notes

Reaction equation

HRID 1789350 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:22]3[NH:26][CH2:25][CH2:24][S:23]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][N:28]=[C:29]=[O:30]>O1CCCC1>[CH3:27][NH:28][C:29]([N:26]1[CH2:25][CH2:24][S:23][CH:22]1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1)=[O:30]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 137680992-{2-[2-(4-Phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine

Product 1

HCID 13767927N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamideYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.69 g of 2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine are dissolved in 40 ml of tetrahydrofuran, and 0.62 g of methyl isocyanate is added thereto at room temperature. The mixture is stirred at the same temperature for 2 hours. The mixture is concentrated under reduced pressure to remove solvent. Water is added to the residue, and crystalline precipitates are collected by filtration. The crystals are washed with ethanol and ether, and then recrystallized from a mixture of ethyl acetate and n-hexane. 3.82 g of N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidin-3-carboxamide are obtained. Yield: 89.7%.

Workup

  1. customat room temperature
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove solvent
  4. additionWater is added to the residue
  5. customcrystalline precipitates
  6. filtrationare collected by filtration
  7. washThe crystals are washed with ethanol and ether
  8. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-cf2b730c091b4f5fb5ea937a4065d490
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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