Dimethyl Sulfoxide → HCID 68778492, compound

HRID 2263077Notes

Reaction equation

HRID 2263077 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([NH:10][C:11](=[O:18])OCC(Cl)(Cl)Cl)=[CH:8][N:7]=[CH:6][N:5]=1)[CH3:2].[C:19]1([C:25]2[N:26]=[C:27]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[S:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[CH2:1]([O:3][C:4]1[C:9]([NH:10][C:11]([N:33]2[CH2:34][CH2:35][N:30]([C:27]3[S:28][CH:29]=[C:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:26]=3)[CH2:31][CH2:32]2)=[O:18])=[CH:8][N:7]=[CH:6][N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 86245271HCID 86245271, compound

Product 1

HCID 68778492HCID 68778492, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl (4-ethoxypyrimidin-5-yl)carbamate (315 mg, 1.00 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (245 mg, 1.00 mmol), diisopropylethylamine (0.174 ml, 1.00 mmol) and dimethylsulfoxide (5 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 a mixed solvent of ethyl acetate and hexane to obtain the desired product (177 mg, 43.2%) 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-3aa4e10089bf47d2b4230da21a84a948
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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