Dimethyl Sulfoxide → HCID 68780027, compound

HRID 2263110Notes

Reaction equation

HRID 2263110 reaction equation
[Cl:1][C:2]1[C:3]([CH3:24])=[N:4][O:5][C:6]=1[N:7]([C:16]([O:18]CC(Cl)(Cl)Cl)=O)C(OCC(Cl)(Cl)Cl)=O.[C:25]1([C:31]2[N:32]=[C:33]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[S:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[Cl:1][C:2]1[C:3]([CH3:24])=[N:4][O:5][C:6]=1[NH:7][C:16]([N:39]1[CH2:40][CH2:41][N:36]([C:33]2[S:34][CH:35]=[C:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:32]=2)[CH2:37][CH2:38]1)=[O:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 86625497HCID 86625497, compound

Product 1

HCID 68780027HCID 68780027, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of bis(2,2,2-trichloroethyl) (4-chloro-3-methylisoxazol-5-yl)imidodicarbonate (200 mg, 0.418 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (204 mg, 0.836 mmol), diisopropylethylamine (0.144 ml, 0.836 mmol) and dimethylsulfoxide (4 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 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 (123 mg, 73.2%) 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 purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-16b555e91c614dd4bf4e72842bb6abb7
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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