Water → HCID 86598612, compound

HRID 1817130Notes

Reaction equation

HRID 1817130 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-methoxybenzylsulfone 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-e9374572b0dd4dacaef39da954181682
Source dataset
uspto-grants-2009_10
Patent number
US07598232B2

Reaction notes

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