Water → HCID 86598612, compound

HRID 2188730Notes

Reaction equation

HRID 2188730 reaction equation
[CH3:1][O:2][C:3]1[CH:55]=[C:54]([O:56][CH3:57])[CH:53]=[C:52]([O:58][CH3:59])[C:4]=1[CH:5]=[CH:6][CH:7]([S:21]([CH:24]([CH:38]=[CH:39][C:40]1[C:45]([O:46][CH3:47])=[CH:44][C:43]([O:48][CH3:49])=[CH:42][C:41]=1[O:50][CH3:51])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([NH:33][C:34](=[O:37])[CH2:35]Cl)[CH:26]=1)(=[O:23])=[O:22])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH:16][C:17](=[O:20])[CH2:18]Cl)[CH:9]=1.[CH3:60][N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:55]=[C:54]([O:56][CH3:57])[CH:53]=[C:52]([O:58][CH3:59])[C:4]=1/[CH:5]=[CH:6]/[CH:7]([S:21]([CH:24](/[CH:38]=[CH:39]/[C:40]1[C:45]([O:46][CH3:47])=[CH:44][C:43]([O:48][CH3:49])=[CH:42][C:41]=1[O:50][CH3:51])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([NH:33][C:34](=[O:37])[CH2:35][N:64]2[CH2:65][CH2:66][N:61]([CH3:60])[CH2:62][CH2:63]2)[CH:26]=1)(=[O:23])=[O:22])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH:16][C:17](=[O:20])[CH2:18][N:64]2[CH2:65][CH2:66][N:61]([CH3:60])[CH2:62][CH2:63]2)[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 66912773HCID 66912773, compound

Product 1

HCID 86598612HCID 86598612, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4,6-trimethoxystyryl-3-(chloroacetamido)-4-methoxybenzyl sulfone (example 7) (10 mmol), N-methylpiperazine (10 mmol) and potassium carbonate (10 mmol) in dimethylformamide (20 mL) was refluxed for 5 h at 80° C. The reaction mixture was cooled to room temperature, and water was added. The solution was then extracted with ethyl acetate and organic layer was washed with water, brine and dried over sodium sulfate. Evaporation of the solvent in a rotary evaporator gave (E)-2,4,6-trimethoxystyryl-3-[(4-methylpiperazinyl)acetamido]-4-methoxy-benzylsulfone in 87% yield. m.p. 176-178° C.

Workup

  1. extractionThe solution was then extracted with ethyl acetate and organic layer
  2. washwas washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the solvent
  5. customin a rotary evaporator

Sources & evidence

ORD record
ord-90bc1267e9c04626ba6b30401d2171ba
Source dataset
uspto-grants-2012_12
Patent number
US08324190B2

Reaction notes

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