Dimethyl Sulfoxide → HCID 68779916, compound

HRID 2263076Notes

Reaction equation

HRID 2263076 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)=[CH:3][N:2]=1.[C:16]1([C:22]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[S:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:16]1([C:22]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][N:30]([C:8]([NH:7][C:4]4[CH:5]=[CH:6][N:1]=[N:2][CH:3]=4)=[O:15])[CH2:29][CH2:28]3)[S:24][N:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 68777872HCID 68777872, compound

Product 1

HCID 68779916HCID 68779916, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl pyridazin-4-ylcarbamate (100 mg, 0.370 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (88.9 mg, 0.370 mmol), diisopropylethylamine (0.0645 ml, 0.370 mmol) and dimethylsulfoxide (2 ml) was stirred at 70° C. for 12 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 and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate to obtain the desired product (55.0 mg, 40.4%) 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 recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-91c5d5ce2ff44a7b9df941c68d0d7f25
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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