Sodium Iodide → HCID 23206543, compound

HRID 1289424Notes

Reaction equation

HRID 1289424 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[Cl:15][C:16]([Cl:23])([Cl:22])[CH2:17][O:18][C:19](Cl)=[O:20].[CH2:24]([O:26][P:27]([O:31]CC)[O:28][CH2:29][CH3:30])[CH3:25].[I-].[Na+]>C(#N)C>[CH2:24]([O:26][P:27]([CH:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[N:9]1[C:19]([O:18][CH2:17][C:16]([Cl:23])([Cl:22])[Cl:15])=[O:20])(=[O:31])[O:28][CH2:29][CH3:30])[CH3:25]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 31215Triethyl phosphiteHCID 870632,2,2-Trichloroethyl chloroformateHCID 126475676-(Trifluoromethyl)quinoline

Product 1

HCID 23206543HCID 23206543, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

41.4 g of 6-trifluoromethylquinoline is introduced into 250 ml of acetonitrile at 0° C. 29 ml of chloroformic acid-2,2,2-trichloroethyl ester is rapidly instilled and the mixture is stirred for 30 minutes. 36.4 ml of triethylphosphite is instilled and 49.8 g of sodium iodide is added in portions. It is heated for 10 minutes to 50° C., the solution is concentrated by evaporation, mixed with 400 ml of water and extracted four times with 400 ml of ethyl acetate each. The crude product is purified by column chromatography and recrystallized from isopropyl ether.

Workup

  1. temperatureIt is heated for 10 minutes to 50° C.
  2. concentrationthe solution is concentrated by evaporation
  3. additionmixed with 400 ml of water
  4. extractionextracted four times with 400 ml of ethyl acetate each
  5. customThe crude product is purified by column chromatography
  6. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-234356a5b0f6420ba5dd3c2eea3f6b30
Source dataset
uspto-grants-1998_05
Patent number
US05750526

Reaction notes

Loading…