Potassium Carbonate → HCID 60207303, compound

HRID 1192038Notes

Reaction equation

HRID 1192038 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[SH:6].Cl[C:8]1[S:12][C:11]([C:13](=[O:15])[CH3:14])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O>[N+:16]([C:9]1[CH:10]=[C:11]([C:13](=[O:15])[CH3:14])[S:12][C:8]=1[S:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-oneHCID 178527881HCID 178527881, compound

Product 1

HCID 60207303HCID 60207303, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of thiazole-2-thiol (0.05 g, 0.5 mmol) in toluene (10ML), was added 1-(5-Chloro-4-nitro-2-thienyl)ethanone (0.102 g, 0.5 mmol) and K2CO3 (0.69 g, 5 mmol). The resulting reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with water (10 mL) and was extracted with ethyl acetate. The organic extract was dried (Na2SO4), concentrated under vacuum and the residue purified by silica gel chromatography using a mixture of 70:30 ethyl acetate and hexane as eluent to afford the title product as a solid (60 mg, 43% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.51 (2H, s), 8.26 (2H, dd), 8.23 (2H, dd), 2.54 (3H, s). MS m/z: 287.9 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customthe residue purified by silica gel chromatography
  7. additiona mixture of 70:30 ethyl acetate and hexane as eluent

Sources & evidence

ORD record
ord-22596d45babd4d949955ab025a95008f
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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