Ammonium Chloride → HCID 67059736, compound

HRID 1671293Notes

Reaction equation

HRID 1671293 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.CON(C)[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>O1CCCC1.C([N-]C(C)C)(C)C.[Li+]>[F:1][C:2]1[C:7]([C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:19])=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 739342,6-DifluoropyridineHCID 569575N-Methoxy-N-methylbenzamide

Product 1

HCID 67059736HCID 67059736, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724682Lithium diisopropylamideSolvent

Procedure

To a solution of 2,6-difluoropyridine (1.0 g, manufactured by Tokyo Chemical Industry Co., Ltd.) in tetrahydrofuran (40 mL, manufactured by Kanto Chemical Co., Inc.), lithium diisopropylamide (23% solution in tetrahydrofuran/ethylbenzene/heptane, 5.79 mL, manufactured by Sigma-Aldrich Corp.) was added dropwise at −78° C., and the mixture was stirred for 30 minutes. Subsequently, N-methoxy-N-methylbenzamide (1.46 mL, manufactured by Sigma-Aldrich Corp.) was further added at the same temperature, and while the temperature was gradually raised to room temperature, the mixture was stirred overnight. A saturated aqueous solution of ammonium chloride (30 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (3×30 mL), washed with brine (30 mL), and dried (MgSO4). The solvent was then evaporated, to give 1.90 g of the title compound. LC-MS: HPLC retention time 1.63 minutes, m/z (M−F+OMe) 232, condition C-1.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  3. washwashed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-416499b1117b454c87c7f5c4ee734589
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

Loading…