Ethoxalyl chloride → Ethyl [(3-chloro-2,6-difluorophenyl)carbamoyl]formate

HRID 1396333Notes

Reaction equation

HRID 1396333 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([C:6]([F:9])=[CH:7][CH:8]=1)[NH2:5].Cl[C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1>[Cl:1][C:2]1[C:3]([F:10])=[C:4]([NH:5][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:18])[C:6]([F:9])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 177507453-Chloro-2,6-difluoroaniline

Product 1

HCID 123515043Ethyl [(3-chloro-2,6-difluorophenyl)carbamoyl]formateYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-2,6-difluoroaniline (430 mg, 2.55 mmol) and TEA (0.5 mL, 3.59 mmol) in THF (5 mL) was added ethyl 2-chloro-2-oxoacetate (0.3 mL, 2.63 mmol). A white precipitate was formed immediately. After 30 min, the reaction mixture was filtered and rinsed with ether. The filtrate was concentrated to yield a crude yellow oil, which was purified by silica gel chromatography to yield the desired product (484 mg, 72%) as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.42 (br. s., 1H), 7.35 (m, 1H), 6.98 (m, 1H), 4.45 (q, J=7.2 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H). MS (ESI) m/z: 263.9 (M+H)+.

Workup

  1. customA white precipitate was formed immediately
  2. filtrationthe reaction mixture was filtered
  3. washrinsed with ether
  4. concentrationThe filtrate was concentrated
  5. customto yield a crude yellow oil, which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-468de7c5843d466189b4ee58e640f275
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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