Ammonium Chloride → HCID 58542355, compound

HRID 1951898Notes

Reaction equation

HRID 1951898 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]([C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)([CH3:11])[CH:9]=[O:10])([CH3:4])([CH3:3])[CH3:2].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][C:22]=1[F:29].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]([C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)([CH3:11])[CH:9]([C:24]1[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([F:29])[CH:23]=1)[OH:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58542343HCID 58542343, compoundHCID 178505943HCID 178505943, compound

Product 1

HCID 58542355HCID 58542355, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A tetrahydrofuran (20 ml) solution of the compound (6.47 g, 22.7 mmol) obtained in Step 3 above was added dropwise to 4-chloro-3-fluorophenyl magnesium bromide (0.5 M tetrahydrofuran solution) (100 ml, 50.0 mmol) under ice cooling and the resulting mixture was stirred at the same temperature for 1 hour. An aqueous solution of saturated ammonium chloride was added to the reaction mixture to terminate the reaction, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. An n-hexane/ethyl acetate mixed solvent was added to the residue obtained and the resulting precipitate was collected by filtration and dried to give the title compound (7.92 g, 84%) as a white solid.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionAn n-hexane/ethyl acetate mixed solvent was added to the residue
  7. customobtained
  8. filtrationthe resulting precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-e4eb003898304347bb3aa8470a9af75d
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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