Water → (2,4-Dichlorophenyl)[2-nitro-4-(E-((4-acetylpiperazin-1-yl)carbonyl)ethenyl)phenyl]sulfide

HRID 1792639Notes

Reaction equation

HRID 1792639 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=1[SH:38].O>CN(C=O)C>[Cl:30][C:31]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=1[S:38][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 707302,4-DichlorobenzenethiolHCID 10664709(E)-1-(4-acetylpiperazin-1-yl)-3-(4-chloro-3-nitrophenyl)prop-2-en-1-one

Product 1

HCID 9847995(2,4-Dichlorophenyl)[2-nitro-4-(E-((4-acetylpiperazin-1-yl)carbonyl)ethenyl)phenyl]sulfideYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-chloro-3-nitro-cinnamide (275 mg, 0.814 mmol) from Example 32A in 1.0 mL of DMF was added potassium carbonate (169 mg, 1.22 mmol), followed by the dropwise addition of 2,4-dichlorothiophenol (146 mg, 0.815 mmol). The mixture was then stirred at room temperature for 60 minutes. Completion of the reaction was indicated by the TLC. Water was then added to precipitate the product. Filtration, washing with cold water, and drying in a vacuum oven afforded 350 mg (0.728 mmol, 89%) of the titled title compound as a light yellow solid. 1H NMR (d6-DMSO, 300 MHz) δ 2.05 (s, 3H), 3.42-3.50 (br m, 4H), 3.50-3.64 (br m, 2H), 3.64-3.79 (br m, 2H), 6.83 (d, J=8.7 Hz, 1H), 7.44 (d, J=15.3 Hz, 1H), 7.55 (d, J=15.3 Hz, 1H), 7.63 (dd, J=2.7, 8.7 Hz, 1H), 7.83 (d, J=8.7 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.96 (d, J=2.7 Hz, 1H), 8.69 (d, J=1.8 Hz, 1H). MS (DCI/NH3) (M+H)+ at m/z 497, 499, 501. Analysis calculated for C21H19N3O4Cl2S1.0.82H2O: C, 50.94; H, 4.20; N, 8.49. Found: C, 50.91; H, 4.21; N, 8.69.

Workup

  1. customto precipitate the product
  2. filtrationFiltration
  3. washwashing with cold water
  4. customdrying in a vacuum oven

Sources & evidence

ORD record
ord-261154201d0b4099a95e900f1888b4e8
Source dataset
uspto-grants-2006_07
Patent number
USRE039197E1

Reaction notes

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