Sodium Thiosulfate → HCID 59432212, compound

HRID 506494Notes

Reaction equation

HRID 506494 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]\[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[C:17]([N+:25]([O-])=O)[CH:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O.O>[CH3:12][O:11][C:7]1[CH:6]=[C:5](/[CH:13]=[CH:14]\[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:23])[F:24])=[C:17]([NH2:25])[CH:16]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 24477Sodium ThiosulfateHCID 67023764HCID 67023764, compound

Product 1

HCID 59432212HCID 59432212, compoundYield 68.6%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
50 °C

Procedure

4.1 grams (10.8 mmol) of (Z)-1-(3,4,5-trimethoxyphenyl)-2-(3′-nitro-4′-difluoromethoxy-phenyl)ethene was dissolved in 10 ml of acetone/water (V/V, 2:1). The mixture was heated to 50°C., and was stirred to dissolve all the solid. 18.8 grams of sodium thiosulphate was added and the reaction mixture was heated to reflux for 6 hours. The reaction was monitored by TLC. After the reaction was completed, the reaction mixture was cooled to room temperature. The organic layer was separated, and the water layer was extracted with 50 ml×4 of ethyl acetate. The organic layer was combined and was washed with saturated brine, and then was dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporator partially and then cooled to get crude product. The crude product was recrystallized from petroleum ether to give 2.6 grams of yellowish crystalline solid in a yield of 68.6%. 1H-NMR (ppm) δ: 7.08 (d, 1H, 2′-H), 6.92 (dd, 1H, 6′-H), 6.76 (d, 1H, 5′-H), 6.62 (s, 2H, 2,6-H), 6.49 (d, 1H, 1a-H), 6.43 (d, 1H, 1a′-H), 6.28 (t, 1H, J2H-F=72 Hz, —CHF2), 5.13 (broad, 2H, NH2), 3.86 (s, 3H, 4-OCH3), 3.70 (s, 6H, 3,5-OCH3).

Workup

  1. dissolutionto dissolve all the solid
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 6 hours
  4. temperaturethe reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. extractionthe water layer was extracted with 50 ml×4 of ethyl acetate
  7. washwas washed with saturated brine
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. customThe solvent was removed by rotary evaporator partially
  10. temperaturecooled
  11. customto get crude product
  12. customThe crude product was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-a770dd7e077b42fcb18a6e9e0ae448d6
Source dataset
uspto-grants-2010_08
Patent number
US07786098B2

Reaction notes

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