Ammonium Chloride → HCID 67040739, compound

HRID 605141Notes

Reaction equation

HRID 605141 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24](=[O:33])[NH:25][C:26]4[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=4)=[CH:20][C:19]=3[N+:34]([O-])=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>O.C(O)C.[Fe]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24](=[O:33])[NH:25][C:26]4[CH:27]=[CH:28][C:29]([Br:32])=[CH:30][CH:31]=4)=[CH:20][C:19]=3[NH2:34])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67040183HCID 67040183, compound

Product 1

HCID 67040739HCID 67040739, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product of Example 93C (517 mg, 0.936 mmol), iron powder (322 mg, 5.76 mmol), and ammonium chloride (328 mg, 6.13 mmol) in water (3 mL) and ethanol (6 mL) were heated at 90° for 30 minutes. The hot reaction mixture was vacuum filtered and the residue washed with methanol and ethyl acetate. The filtrate was concentrated by rotary evaporation under vacuum, the residue partitioned with water (50 mL) and ethyl acetate (100 mL), and the organic phase washed with water (2×50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under vacuum to provide the title compound as an off-white foam (325 mg, 66%).

Workup

  1. filtrationfiltered
  2. washthe residue washed with methanol and ethyl acetate
  3. concentrationThe filtrate was concentrated by rotary evaporation under vacuum
  4. customthe residue partitioned with water (50 mL) and ethyl acetate (100 mL)
  5. washthe organic phase washed with water (2×50 mL) and brine (50 mL)
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation under vacuum

Sources & evidence

ORD record
ord-92c4171546194c13ab7ded30378c5411
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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