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

HRID 2262953Notes

Reaction equation

HRID 2262953 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.[CH2:25]1[O:33][C:32]2[CH:31]=[CH:30][C:29]([N:34]=[C:35]=[O:36])=[CH:28][C:27]=2[O:26]1>O1CCCC1>[O:33]1[C:32]2[CH:31]=[CH:30][C:29]([NH:34][C:35]([N:15]3[CH2:16][CH2:17][N:12]([C:10]4[S:9][N:8]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[N:11]=4)[CH2:13][CH2:14]3)=[O:36])=[CH:28][C:27]=2[O:26][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 52232135-Isocyanato-1,3-dioxaindane

Product 1

HCID 68777311N-1,3-Benzodioxol-5-yl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 71.9%

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 3,4-(methylenedioxy)phenyl isocyanate (199 mg, 1.22 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 239 mg (71.9%) of the desired product as a solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customThe residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-4acfe02b86f54d3c914265aff0a52f2b
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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