Ethyl Acetate → HCID 21061257, compound

HRID 1241903Notes

Reaction equation

HRID 1241903 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([SH:13])[S:11][CH:12]=2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:25]=[C:26]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([NH:34][C:35](=[O:38])[CH2:36]Cl)[CH2:30][CH2:29]1.C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([S:13][CH2:36][C:35]([NH:34][CH:31]3[CH2:30][CH2:29][N:28]([CH2:27][C:26]4[CH:39]=[CH:40][C:41]([Cl:42])=[C:24]([Cl:23])[CH:25]=4)[CH2:33][CH2:32]3)=[O:38])[S:11][CH:12]=2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21937184HCID 21937184, compoundHCID 178526465HCID 178526465, compound

Product 1

HCID 21061257HCID 21061257, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Chloro-3-nitrophenyl)-2-mercaptothiazole (0.5 g) was dissolved in dimethylformamide (20 mL), and potassium carbonate (0.7 g) was added to the solution. Then, N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]chloroacetamide (0.6 g) was added, and the mixture was stirred at room temperature for 3 hrs. Ethyl acetate was added to the reaction mixture, washed with water and saturated brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to give the title compound (0.7 g) as a yellow solid.

Workup

  1. washwashed with water and saturated brine
  2. customdried
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-5f944f31e2db47fbb4315dba44971899
Source dataset
uspto-grants-2006_10
Patent number
US07115635B2

Reaction notes

Loading…