Ammonium Chloride → HCID 9816246, compound

HRID 1934351Notes

Reaction equation

HRID 1934351 reaction equation
[CH:1]([C:3]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:5])[CH3:4])=[O:2].[CH3:17][Mg]Br.[Cl-].[NH4+]>C1COCC1>[OH:2][CH:1]([CH3:17])[C:3]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 9794544HCID 9794544, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 9816246HCID 9816246, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(1-formyl-1-methylethyl)-2,4-difluorobenzamide obtained in Example 32 (1.14 g, 5 mmol) in THF (10 ml) was added 0.9 M methyl magnesium bromide in THF (13 ml, 12 mmol) dropwise at −20° C. The reaction mixture was warmed gradually to room temperature over 2 hours and added to 10% aqueous ammonium chloride (100 ml). The resulting mixture was extracted with ethyl acetate, washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, concentrated under a reduced pressure and the residue was crystallized from hexane/ethyl acetate to give the title compound (1.05 g; 86%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washwashed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under a reduced pressure
  5. customthe residue was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-a6b2ecf4a0b54ea897b9aefd8cc9c65f
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

Loading…