Trifluoroacetic acid → 5-(2-Chloroethyl)-6-chlorooxindole

HRID 503817Notes

Reaction equation

HRID 503817 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Cl:14])[NH:10][C:9](=[O:15])[CH2:8]2)=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[Cl:1][CH2:2][CH2:3][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Cl:14])[NH:10][C:9](=[O:15])[CH2:8]2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 37309465-chloroacetyl-6-chlorooxindole

Product 1

HCID 106094745-(2-Chloroethyl)-6-chlorooxindoleYield 92.2%

Conditions

Temperature
42.5 °C

Procedure

A mixture of 130 g of 5-(2-chloroacetyl)-6-chlorooxindole, 455 ml of trifluoroacetic acid and 148.6 g of triethylsilane was maintained at a temperature of about 40-45° C. for 7 hours. The reaction mass was filtered at −5 to 0° C. after maintaining for 1 to 2 hours at the same temperature. The compound was washed with 130 ml of water and further slurried in 650 ml of water. After separation from the water, it was then dried to yield 113 g of the title compound.

Workup

  1. filtrationThe reaction mass was filtered at −5 to 0° C.
  2. temperatureafter maintaining for 1 to 2 hours at the same temperature
  3. washThe compound was washed with 130 ml of water and further slurried in 650 ml of water
  4. customAfter separation from the water, it
  5. customwas then dried

Sources & evidence

ORD record
ord-6dc5fda829294e978156d1043442b08f
Source dataset
uspto-grants-2010_08
Patent number
US07777037B2

Reaction notes

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