Water → N-(5-ethyl-1,3,4-oxadiazol-2-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2262952Notes

Reaction equation

HRID 2262952 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([NH:8][C:9](=[O:16])OCC(Cl)(Cl)Cl)=[N:5][N:4]=1)[CH3:2].[C:17]1([C:23]2[N:27]=[C:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:25][N:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH2:1]([C:3]1[O:7][C:6]([NH:8][C:9]([N:31]2[CH2:32][CH2:33][N:28]([C:26]3[S:25][N:24]=[C:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:27]=3)[CH2:29][CH2:30]2)=[O:16])=[N:5][N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 862451962,2,2-Trichloroethyl (5-ethyl-1,3,4-oxadiazol-2-yl)carbamate

Product 1

HCID 68777817N-(5-ethyl-1,3,4-oxadiazol-2-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl (5-ethyl-1,3,4-oxadiazol-2-yl)carbamate (213 mg, 0.738 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.129 ml, 0.738 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 3 hours and half. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Chloroform was poured to the residue, and 140 mg (49.1%) of the desired product as a solid was separated by filtration.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionChloroform was poured to the residue, and 140 mg (49.1%) of the desired product as a solid
  6. customwas separated by filtration

Sources & evidence

ORD record
ord-31d8a92e0f9845988ec2b84ac1510c4f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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