Triethylsilane → 5-(2-Chloroethyl)-6-chlorooxindole

HRID 1822100Notes

Reaction equation

HRID 1822100 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[CH:12](O)[CH2:13][Cl:14].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[CH2:12][CH2:13][Cl:14]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 16128890HCID 16128890, compound

Product 1

HCID 106094745-(2-Chloroethyl)-6-chlorooxindoleYield 100.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A 2 L round-bottom flask is loaded with 300 g (1.22 mols) of 6-chloro-5-(2-chloro-1-hydroxy-ethyl)-1,3-dihydro-indol-2-one and 1140 ml of trifluoroacetic acid, under nitrogen atmosphere. The mixture is stirred at room temperature for 1 h, then heated to about 35-40° C. 214 ml (1.34 mols) of triethylsilane are then dropped therein in approx. 1 hr 30 min, keeping stirring for 12-14 h. Separately, a round-bottom flask is loaded with 3000 g of a water/ice mixture and the reaction mixture is carefully dropped therein, in about 1 hr 30 min, under strong stirring. The resulting white suspension is stirred for 30 min, then filtered, washed with purified water (4×500 ml) and heptane (400 ml), then dried at 60° C. under vacuum to afford 281 g of 6-chloro-5-(2-chloro-ethyl)-1,3-dihydro-indol-2-one.

Workup

  1. temperatureheated to about 35-40° C
  2. waitin approx. 1 hr 30 min
  3. stirringkeeping stirring for 12-14 h
  4. additionthe reaction mixture is carefully dropped
  5. waitin about 1 hr 30 min
  6. stirringThe resulting white suspension is stirred for 30 min
  7. filtrationfiltered
  8. washwashed with purified water (4×500 ml) and heptane (400 ml)
  9. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-9e9a28cac672496b8725c5ab12739d9f
Source dataset
uspto-grants-2009_10
Patent number
US07608711B2

Reaction notes

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