Ethyl chloroformate → HCID 18615633, compound

HRID 277415Notes

Reaction equation

HRID 277415 reaction equation
[Cl:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13]>N1C=CC=CC=1>[Cl:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH:6][C:12](=[O:13])[O:14][CH2:15][CH3:16])=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 146245254-Chloro-2,5-difluoroaniline

Product 1

HCID 18615633HCID 18615633, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chloro-2,5-difluoroaniline (XXXIX) (2.1 g, 12.8 mmol) was mixed with pyridine (20 ml) at 0° C., to it was dropwise added ethyl chloroformate (1.5 g, 13.8 mmol). After stirring for 2.5 hr while temperature slowly raised to room temperature, pyridine was evaporated and the residue crystallized in ice-water (100 ml). The crystals were filtered, washed with water and dried in fume hood overnight (2.7 g). 1H NMR (CDCl3, 300 MHz) 1.33 (3H, t, J=7.1 Hz), 4.23 (2H, q, J=7.1 Hz), 6.89 (1H, br), 7.12 (1H, dd, J=6.5, 6.5 Hz), 8.05 (1H, dd, J=7.8, 9.6 Hz) ppm.

Workup

  1. custompyridine was evaporated
  2. customthe residue crystallized in ice-water (100 ml)
  3. filtrationThe crystals were filtered
  4. washwashed with water
  5. customdried in fume hood overnight (2.7 g)

Sources & evidence

ORD record
ord-5c6780738622468b9e8029b0bfee6d78
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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