Water → HCID 87201917, compound

HRID 1817128Notes

Reaction equation

HRID 1817128 reaction equation
[CH3:1][O:2][C:3]1[CH:75]=[C:74]([O:76][CH3:77])[CH:73]=[C:72]([O:78][CH3:79])[C:4]=1/[CH:5]=[CH:6]/[CH:7]([S:31]([CH:34](/[CH:58]=[CH:59]/[C:60]1[C:65]([O:66][CH3:67])=[CH:64][C:63]([O:68][CH3:69])=[CH:62][C:61]=1[O:70][CH3:71])[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([NH:43][C:44](=[O:57])[C:45]2[CH:50]=[C:49]([N+:51]([O-])=O)[CH:48]=[C:47]([N+:54]([O-])=O)[CH:46]=2)[CH:36]=1)(=[O:33])=[O:32])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[C:20]([N+:27]([O-])=O)[CH:19]=2)[CH:9]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].O>O.CC(C)=O>[CH3:79][O:78][C:72]1[CH:73]=[C:74]([O:76][CH3:77])[CH:75]=[C:3]([O:2][CH3:1])[C:4]=1/[CH:5]=[CH:6]/[CH:7]([S:31]([CH:34](/[CH:58]=[CH:59]/[C:60]1[C:61]([O:70][CH3:71])=[CH:62][C:63]([O:68][CH3:69])=[CH:64][C:65]=1[O:66][CH3:67])[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([NH:43][C:44](=[O:57])[C:45]2[CH:50]=[C:49]([NH2:51])[CH:48]=[C:47]([NH2:54])[CH:46]=2)[CH:36]=1)(=[O:32])=[O:33])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH:16][C:17](=[O:30])[C:18]2[CH:19]=[C:20]([NH2:27])[CH:21]=[C:22]([NH2:24])[CH:23]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 86598611HCID 86598611, compound

Product 1

HCID 87201917HCID 87201917, 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-(3,5-dinitrobenzamido)-4-methoxybenzylsulfone (example 5) (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 yield pure (E)-2,4,6-trimethoxystyryl-3-(3,5,diaminobenzamido)-4-methoxybenzylsulfone. m.p. 208-210° C. NMR (DMSO-d6) δ 3.76(s, 3H), 3.80(s, 6H), 3.82(s, 3H), 4.4(s, 2H), 5.9(s, 1H), 6.2(s, 2H), 7.05-8.26(m, aromatic), 8.85(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-047c350de0a8402694244ea27fa47859
Source dataset
uspto-grants-2009_10
Patent number
US07598232B2

Reaction notes

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