Hydrochloric Acid → HCID 86745342, compound

HRID 1647019Notes

Reaction equation

HRID 1647019 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([C:18](=[O:20])[CH3:19])[C:13](=[O:21])[CH2:12]3)[CH:5]=[C:4]([F:22])[C:3]=1[C:23]([F:26])([F:25])[F:24].[H-].[Na+].Br[CH2:30][CH2:31]Br.Cl>CS(C)=O.CCOCC.O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([C:18](=[O:20])[CH3:19])[C:13](=[O:21])[C:12]23[CH2:31][CH2:30]2)[CH:5]=[C:4]([F:22])[C:3]=1[C:23]([F:26])([F:25])[F:24]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 86745340HCID 86745340, compound

Product 1

HCID 86745342HCID 86745342, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy]-1-acetyl-2-indolinone (5.1 g, 12.7 mmol) in dimethylsulfoxide is treated with sodium hydride (1.12 g, 27.9 mmol) portionwise over a 30 minute period, treated dropwise with a solution of 1,2-dibromoethane (2.62 g, 14.0 mmol) in dimethylsulfoxide over a 1 hour period and stirred at room temperature until reaction is complete by thin layer chromatography. The reaction mixture is poured into a mixture of water and ether, treated with 10% HCl and separated. The organic phase is washed with water, dried (MgSO4) and concentrated in vacuo to give a residue. The residue is chromatographed on silica gel using 5-10% ethyl acetate in hexane to give the title product as a pale yellow solid, 1.1 g, (20%), mp 118.5°-121° C., identified by 1HNMR.

Workup

  1. customseparated
  2. washThe organic phase is washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe residue is chromatographed on silica gel using 5-10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-625fd3e0ce1b4372b3888bcf760f0633
Source dataset
uspto-grants-1993_01
Patent number
US05182397

Reaction notes

Loading…