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Dimethyl Sulfoxide → N-1,2-Benzisoxazol-3-yl-3-methyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2263052
Notes
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Reaction equation

HRID 2263052 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[S:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=1.[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]([N:28](C(OCC(Cl)(Cl)Cl)=O)[C:29](OCC(Cl)(Cl)Cl)=[O:30])=[N:20]1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]([NH:28][C:29]([N:6]2[CH2:5][CH2:4][N:3]([C:8]3[S:12][N:11]=[C:10]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:9]=3)[CH:2]([CH3:1])[CH2:7]2)=[O:30])=[N:20]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 687761702-Methyl-1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazineHCID 86625471Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate

Product 1

HCID 59594515N-1,2-Benzisoxazol-3-yl-3-methyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Procedure

A solution of 2-methyl-1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (390 mg, 1.50 mmol), bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate (363 mg, 0.750 mmol), diisopropylethylamine (0.131 ml, 0.750 mmol) and dimethylsulfoxide (10 ml) was stirred at 70° C. for 2 hours, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the desired product as a solid. This was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (220 mg, 69.8%) as a solid.

Workup

  1. extractionthe mixture 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. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-55fc659aeb16474ebb2553012b192bd5
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851473B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes