Dimethyl Sulfoxide → N-{4-[Acetyl(methyl)amino]phenyl}-4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

HRID 2263102Notes

Reaction equation

HRID 2263102 reaction equation
[C:1]([N:4]([CH3:20])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:21]1([C:27]2[N:28]=[C:29]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[S:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:1]([N:4]([CH3:20])[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([N:35]2[CH2:36][CH2:37][N:32]([C:29]3[S:30][CH:31]=[C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:28]=3)[CH2:33][CH2:34]2)=[O:19])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 866254962,2,2-Trichloroethyl {4-[acetyl(methyl)amino]phenyl}carbamate

Product 1

HCID 68778453N-{4-[Acetyl(methyl)amino]phenyl}-4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamideYield 31.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl {4-[acetyl(methyl)amino]phenyl}carbamate (200 mg, 0.589 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (144 mg, 0.589 mmol), diisopropylethylamine (0.103 ml, 0.589 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 recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (80.0 mg, 31.3%) 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-645ebb14cd824306b02ad1dd99764c76
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…