Dimethyl Sulfoxide → HCID 68780495, compound

HRID 2263084Notes

Reaction equation

HRID 2263084 reaction equation
[CH3:1][N:2]1[C:6]([N:7]([C:16]([O:18]CC(Cl)(Cl)Cl)=O)C(OCC(Cl)(Cl)Cl)=O)=[CH:5][CH:4]=[N:3]1.[C:24]1([C:30]2[N:31]=[C:32]([N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[S:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[CH3:1][N:2]1[C:6]([NH:7][C:16]([N:38]2[CH2:39][CH2:40][N:35]([C:32]3[S:33][CH:34]=[C:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:31]=3)[CH2:36][CH2:37]2)=[O:18])=[CH:5][CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 86625493HCID 86625493, compound

Product 1

HCID 68780495HCID 68780495, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of bis(2,2,2-trichloroethyl) (1-methyl-1H-pyrazol-5-yl)imidodicarbonate (200 mg, 0.447 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (180 mg, 0.734 mmol), diisopropylethylamine (0.129 ml, 0.734 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. The solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (54.8 mg, 33.2%) 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 a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-13aef3dcb18b4707aac70157c1cde0de
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…