Water → (E)-2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)aniline

HRID 1183216Notes

Reaction equation

HRID 1183216 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][S:8](/[CH:11]=[CH:12]/[C:13]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])(=[O:10])=[O:9])=[CH:5][C:4]=1[N+:27]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].O>CC(C)=O.O>[CH3:24][O:23][C:14]1[CH:15]=[C:16]([O:21][CH3:22])[CH:17]=[C:18]([O:19][CH3:20])[C:13]=1/[CH:12]=[CH:11]/[S:8]([CH2:7][C:6]1[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[C:4]([NH2:27])[CH:5]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 11502726(E)-2,4,6-Trimethoxystyryl 4-Methoxy-3-Nitrobenzyl sulfone

Product 1

HCID 11486204(E)-2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)aniline

Reagents, catalysts & solvents 1

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

Conditions

Temperature
50 °C

Procedure

A solution of 2-((E)-2-(4-methoxy-3-nitrobenzylsulfonyl)vinyl)-1,3,5-trimethoxybenzene (13 mmol) in acetone-water (10:5, 25 mL) was heated to 50° C. After 30 min, sodium hydrosulfite (Na2S2O4, 26.3 mmol) was added slowly, and the mixture was heated at reflux (50° C.) for 1 h. The heated mixture was then cooled to room temperature (25° C.) and water (25 mL) was added. A solid precipitate formed and was separated by filtration. The filtered product was washed with aqueous sodium bicarbonate. The product was distributed between water and ethyl acetate. The ethyl acetate layer was separated and dried over anhydrous sodium sulfate. The ethyl acetate was removed under reduced pressure and the crude product obtained thereby was recrystallized from 2-propanol to yield the desired (E)-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxybenzenamine product. m.p. 148-150° C.

Workup

  1. temperaturethe mixture was heated
  2. additionwas added
  3. customA solid precipitate formed
  4. customwas separated by filtration
  5. washThe filtered product was washed with aqueous sodium bicarbonate
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe ethyl acetate was removed under reduced pressure
  9. customthe crude product obtained
  10. customthereby was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-47beeef67dab498ebd8f3c0fe05ecb3a
Source dataset
uspto-grants-2014_03
Patent number
US08664272B2

Reaction notes

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