Sodium Dithionite → HCID 87497155, compound

HRID 19438Notes

Reaction equation

HRID 19438 reaction equation
[CH3:1][O:2][C:3]1[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[C:47]([O:53][CH3:54])[C:4]=1/[CH:5]=[CH:6]/[CH:7]([S:19]([CH:21](/[CH:33]=[CH:34]/[C:35]1[C:40]([O:41][CH3:42])=[CH:39][C:38]([O:43][CH3:44])=[CH:37][C:36]=1[O:45][CH3:46])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([N+:30]([O-])=O)[CH:23]=1)=[O:20])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([N+:16]([O-])=O)[CH:9]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CC(C)=O.O>[CH3:46][O:45][C:36]1[CH:37]=[C:38]([O:43][CH3:44])[CH:39]=[C:40]([O:41][CH3:42])[C:35]=1/[CH:34]=[CH:33]/[CH:21]([S:19]([CH:7](/[CH:6]=[CH:5]/[C:4]1[C:47]([O:53][CH3:54])=[CH:48][C:49]([O:51][CH3:52])=[CH:50][C:3]=1[O:2][CH3:1])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([NH2:16])[CH:9]=1)=[O:20])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([NH2:30])[CH:23]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 87497523(e)-2,4,6-Trimethoxystyryl-4-methoxy-3-nitrobenzylsulfoxide

Product 1

HCID 87497155HCID 87497155, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

(E)-2,4,6-Trimethoxystyryl-4-methoxy-3-nitrobenzylsulfoxide (1.3 mmol) was dissolved in a 2 to 1mixture of acetone and water (50 mL). The resulting mixture was heated to 50° C. After heating at 50° C. for 30 min, sodium dithionite (26.3 mmol) was added to the heated reaction mixture (portionwise over 20 minutes). The resulting mixture was maintained at 50° C. for 1hour, then cooled to room temperature (25° C.). Water (50 mL) was added to the cooled mixture. The resulting mixture was extracted with ethyl acetate (3×50 mL). The ethyl acetate extracts were combined and washed with saturated aqueous NaHCO3. The ethyl acetate extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield the crude product. The crude product was recrystallized from 2-propanol to afford the desired (E)-2,4,6-trimethoxy styryl-3-amino-4-methoxybenzylsulfoxide, as listed in Table 6.

Workup

  1. temperatureAfter heating at 50° C. for 30 min
  2. temperatureThe resulting mixture was maintained at 50° C. for 1hour
  3. temperaturecooled to room temperature (25° C.)
  4. extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
  5. washwashed with saturated aqueous NaHCO3
  6. extractionThe ethyl acetate extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield the crude product
  11. customThe crude product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-dafb811201a54f49addfd5e8ddc343a5
Source dataset
uspto-grants-2010_06
Patent number
US07744889B2

Reaction notes

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