Ethanol → HCID 89656036, compound

HRID 633546Notes

Reaction equation

HRID 633546 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[N+:15]([O-])=O.[Cl-].[NH4+].O1CCCC1.C(O)C>[Fe].O>[NH2:15][C:6]1[CH:7]=[C:8]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:9]=[CH:10][C:5]=1[O:4][C:3]1[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:2]=1[F:1]

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86721059HCID 86721059, compound

Product 1

HCID 89656036HCID 89656036, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

The product from Example 51A (3.24 g, 9.81 mmol), iron (2.74 g, 49.1 mmol), and ammonium chloride (0.787 g, 14.72 mmol) were combined in the solvent mixture of tetrahydrofuran (21.0 mL), ethanol (21.0 mL) and water (7.0 mL) and heated at 95° C. with vigorous stirring for 3 hours. The mixture was cooled and filtered through a plug of Celite to remove solids. The plug was rinsed repeatedly with methanol and tetrahydrofuran. The filtrate was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated to afford the title compound (2.81 g, 95%).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through a plug of Celite
  3. customto remove solids
  4. washThe plug was rinsed repeatedly with methanol and tetrahydrofuran
  5. concentrationThe filtrate was concentrated
  6. customthe residue partitioned between ethyl acetate and water
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried (anhydrous Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d7daa41a4ad449ccb6c3ef6c5d1ae78d
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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