Triethylamine → HCID 47015344, compound

HRID 538780Notes

Reaction equation

HRID 538780 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[CH3:13][O:14][NH2:15].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([NH:15][O:14][CH3:13])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 5880822,5-Difluorobenzoyl chloride

Product 1

HCID 47015344HCID 47015344, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,5-difluorobenzoyl chloride (1.77 g, 10 mmol) and O-methylhydroxylamine hydrochloride (830 mg, 10 mmol) in methylene chloride (25 mL) at 0° C. was added dropwise triethylamine (2.8 mL, 20 mmol) and the mixture was stirred at room temperature for 8 h. The mixture was then washed with water, brine, dried with MgSO4 and concentrated under reduced pressure. The residue was chromatographed (hexane-EtOAc 2:1) to afford 1.4 g of the title compound. 1H NMR (300 MHz-DMSO-d6) δ 3.70 (s, 3H), 7.42 (m, 3H), 11.64 (s, 1H); MS (DCI/NH3) m/z 188 (M+H)+, 205 (M+NH4)+.

Workup

  1. washThe mixture was then washed with water, brine
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed (hexane-EtOAc 2:1)

Sources & evidence

ORD record
ord-d02ce5ac77064a8eab52e1bd4ed0970b
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

Loading…