Hexane → N-(4-methoxyphenyl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2262912Notes

Reaction equation

HRID 2262912 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1.CCCCCC>O1CCCC1>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([N:15]2[CH2:16][CH2:17][N:12]([C:10]3[S:9][N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:11]=3)[CH2:13][CH2:14]2)=[O:35])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 794431-Isocyanato-4-methoxybenzeneHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine

Product 1

HCID 15980696N-(4-methoxyphenyl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and triethylamine (0.113 ml, 0.812 mmol) in tetrahydrofuran (2 ml) was added 4-methoxyphenyl isocyanate (0.158 ml, 1.22 mmol), and the mixture was stirred at room temperature for 2 hours. To the resulting solution was added hexane (4 ml) and the solid was separated by filtration, which was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate to give 180 mg (56.1%) of the desired product as a solid.

Workup

  1. customthe solid was separated by filtration, which
  2. customwas recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-74e30e11e20545a6ab26bb19ce5218da
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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