Water → HCID 86598614, compound

HRID 2188733Notes

Reaction equation

HRID 2188733 reaction equation
[CH3:1][O:2][C:3]1[CH:69]=[C:68]([O:70][CH3:71])[CH:67]=[C:66]([O:72][CH3:73])[C:4]=1/[CH:5]=[CH:6]/[CH:7]([S:28]([CH:31](/[CH:52]=[CH:53]/[C:54]1[C:59]([O:60][CH3:61])=[CH:58][C:57]([O:62][CH3:63])=[CH:56][C:55]=1[O:64][CH3:65])[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([NH:40][C:41](=[O:51])[C:42]2[CH:47]=[CH:46][C:45]([N+:48]([O-])=O)=[CH:44][CH:43]=2)[CH:33]=1)(=[O:30])=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[CH:9]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].O>O.CC(C)=O>[CH3:73][O:72][C:66]1[CH:67]=[C:68]([O:70][CH3:71])[CH:69]=[C:3]([O:2][CH3:1])[C:4]=1/[CH:5]=[CH:6]/[CH:7]([S:28]([CH:31](/[CH:52]=[CH:53]/[C:54]1[C:59]([O:60][CH3:61])=[CH:58][C:57]([O:62][CH3:63])=[CH:56][C:55]=1[O:64][CH3:65])[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([NH:40][C:41](=[O:51])[C:42]2[CH:43]=[CH:44][C:45]([NH2:48])=[CH:46][CH:47]=2)[CH:33]=1)(=[O:29])=[O:30])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH:16][C:17](=[O:27])[C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 86598615HCID 86598615, compound

Product 1

HCID 86598614HCID 86598614, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A solution of 2,4,6-trimethoxystyryl-3-(4-nitrobenzamido)-4-methoxybenzyl-sulfone (example 10) (1.3 mmol) in acetone water (10:5) was heated to 50° C. After 30 min, sodiumhydrosulfite (Na2S2O4) (26.3 mmol) was added slowly, and the mixture was heated at reflux (50° C., 1 h.), cooled to room temperature and water was added. The product was rinsed with NaHCO3, and then isolated by extraction with ethyl acetate. The organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was recrystallized from 2-propanol to give pure (E)-2,4,6-Trimethoxystyryl-3-(4-aminobenzamido)-4-methoxy-benzylsulfone. m.p. 137-140° C. NMR (DMSO-d6) δ 3.82 (s, 3H), 3.83 (s, 6H), 3.86 (s, 3H), 4.22 (s, 2H), 6.14 (s, 2H), 6.80-8.16 (m, aromatic), 8.60 (s, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperaturecooled to room temperature
  3. washThe product was rinsed with NaHCO3
  4. customisolated by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe crude product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-280b56c51be445299d57baf0360a135a
Source dataset
uspto-grants-2012_12
Patent number
US08324190B2

Reaction notes

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