Triethylamine → HCID 3908440, compound

HRID 1771093Notes

Reaction equation

HRID 1771093 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-f31fe7d5a451435ab810a3017ca5eaa1
Source dataset
uspto-grants-2016_02
Patent number
US09249096B2

Reaction notes

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