Ammonium Chloride → HCID 57779686, compound

HRID 509200Notes

Reaction equation

HRID 509200 reaction equation
FC(F)(F)S([O-])(=O)=O.[CH2:9]([N+:16]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([C:30]([O:32][CH3:33])=[O:31])=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[CH:21]2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>C(O)C.[Zn]>[CH2:9]([N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]([C:30]([O:32][CH3:33])=[O:31])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:29]1=2)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86632441HCID 86632441, compound

Product 1

HCID 57779686HCID 57779686, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of compound 83 (1.05 g, 3.20 mmol) and ammonium chloride (2.67 g, 49.8 mmol) in ethanol (35 mL) was added zinc (2.67 g, 40.8 mmol) and the reaction mixture was heated at 80° C. for 30 minutes then filtered through a pad of Celite®. The solution was diluted with brine, extracted with EtOAc, and the combined organics were dried over, filtered and concentrated to afford compound 84 (0.248 g, 24%) as a white solid after purification by flash chromatography (10 to 40% EtOAc in hexanes). LRMS (ESI): (calc) 329.39 (found) 330.5 (MH)+

Workup

  1. filtrationthen filtered through a pad of Celite®
  2. additionThe solution was diluted with brine
  3. extractionextracted with EtOAc
  4. customthe combined organics were dried over,
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f983aabcdf134686a79c8730c6e80a1d
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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