Ethanol → HCID 69002196, compound

HRID 1821325Notes

Reaction equation

HRID 1821325 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]([C:21]2[S:22][C:23]([N+:26]([O-])=O)=[CH:24][CH:25]=2)=[O:20])=[N:2]1.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:26][C:23]1[S:22][C:21]([C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:20])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 68999165HCID 68999165, compound

Product 1

HCID 69002196HCID 69002196, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Compound 51 (1.5 g, 3.84 mmol), iron powder (4.3 g, 76.8 mmol) and ammonium chloride (616 mg, 11.52 mmol) were added with ethanol (10.0 mL) and water (10.0 mL) at room temperature, stirred at 50° C. for 7 hours and the reaction mixture was filtered through celite. The filtrate was extracted with ethyl acetate and the organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in a mixed solvent of chloroform/ethyl acetate to obtain Compound 56 (724 mg, 52%).

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe organic layer was sequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated in a mixed solvent of chloroform/ethyl acetate

Sources & evidence

ORD record
ord-dbbbc94274344f618cdd20f8f684c539
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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