Water → HCID 46941671, compound

HRID 1188872Notes

Reaction equation

HRID 1188872 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:26]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].O>[Fe].C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[NH2:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 66726067HCID 66726067, compound

Product 1

HCID 46941671HCID 46941671, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(benzyloxy)-4-[4-(methylsulfonyl)phenoxy]-1-nitrobenzene (11.0 g), iron powder (7.6 g), calcium chloride (0.3 g), water (30 mL) and ethanol (120 mL) was stirred at 80° C. for 2 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated. Water was added to the residue, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crude product was crystallized from toluene, and the obtained solid was washed with diethyl ether to give the title compound (9.3 g, yield 92%) as pale-brown crystals. MS 370 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. additionWater was added to the residue
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. washThe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained crude product
  10. customwas crystallized from toluene
  11. washthe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-c5f1ccc0ea8349db91a0cf38e12d952a
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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