Triethylamine → HCID 3908440, compound

HRID 1848376Notes

Reaction equation

HRID 1848376 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.Cl[C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C1COCC1>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 20884Ethoxalyl chloride

Product 1

HCID 3908440HCID 3908440, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-difluoroaniline (10 g, 77 mmol) and triethylamine (12.95 mL, 93.00 mmol) in THF (50 mL) was added ethyl 2-chloro-2-oxoacetate (9.05 mL, 81.0 mmol) drop wise at 0° C. A white solid precipitated instantly. The reaction mixture was stirred at rt for 1 h. The solvent was evaporated, and Et2O was added. The solution was washed with 1N HCl (20 mL), saturated NaHCO3 and then brine, then the organic layer dried over MgSO4, filtered and concentrated to give Intermediate 11A (15.8 g, 68.9 mmol, 89.0% yield) as a white crystalline solid. HPLC/MS (Method L) RT=1.58 min, [M+H]+ 230.0.

Workup

  1. customA white solid precipitated instantly
  2. customThe solvent was evaporated
  3. additionEt2O was added
  4. washThe solution was washed with 1N HCl (20 mL), saturated NaHCO3
  5. dry with materialbrine, then the organic layer dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6413678511e1406f9876fd73fa2697bb
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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