Dimethyl Sulfoxide → HCID 68777445, compound

HRID 2263078Notes

Reaction equation

HRID 2263078 reaction equation
[N:1]1[CH:6]=[C:5]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:4]=[N:3][CH:2]=1.[C:16]1([C:22]2[N:23]=[C:24]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[S:25][CH:26]=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:23]=[C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:8]([NH:7][C:5]4[CH:4]=[N:3][CH:2]=[N:1][CH:6]=4)=[O:15])[CH2:29][CH2:28]3)[S:25][CH:26]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 68778012HCID 68778012, compound

Product 1

HCID 68777445HCID 68777445, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl pyrimidin-5-ylcarbamate (263 mg, 0.972 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (238 mg, 0.972 mmol), diisopropylethylamine (0.169 ml, 0.972 mmol) and dimethylsulfoxide (3 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 (97.4 mg, 27.4%) 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-c0aab37d597048268e9e0bb3a737a63f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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