Ammonium Chloride → HCID 11591742, compound

HRID 545108Notes

Reaction equation

HRID 545108 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:31])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=3)[N:21]=2)[CH2:7]1.[Cl-].[NH4+]>O1CCCC1.CO.[Fe]>[NH2:28][C:24]1[CH:23]=[C:22]([C:20]2[N:21]=[C:17]([S:16][CH2:15][C:14]([NH:13][CH2:12][C@@H:8]3[O:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]4[CH:32]=[CH:33][C:34]([Cl:35])=[C:2]([Cl:1])[CH:3]=4)[CH2:7]3)=[O:31])[S:18][CH:19]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 59009126HCID 59009126, compound

Product 1

HCID 11591742HCID 11591742, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the resultant product (4.65 g) of (6-2) in tetrahydrofuran (24 mL) and methanol (16 mL) was added dropwise to an aqueous (16 mL) suspension of ammonium chloride (2.25 g) and iron powder (1.41 g) at 60° C. The reaction mixture was heated under reflux for 3.5 hrs. After allowing to cool, the reaction mixture was filtered through celite. A 1 mol/L aqueous sodium hydroxide solution was added to the filtrate, and the organic solvent alone was evaporated under reduced pressure. The residue was extracted with ethyl acetate, the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (3.87 g) as a pale-yellow amorphous solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3.5 hrs
  3. temperatureto cool
  4. filtrationthe reaction mixture was filtered through celite
  5. additionA 1 mol/L aqueous sodium hydroxide solution was added to the filtrate
  6. customthe organic solvent alone was evaporated under reduced pressure
  7. extractionThe residue was extracted with ethyl acetate
  8. washthe extract was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography
  12. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-fe56c065da3c489bad8f23ebe1a7909e
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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