Isatin → HCID 19600971, compound

HRID 610076Notes

Reaction equation

HRID 610076 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[F:12][C:13]([F:17])([F:16])[CH2:14]I>O>[F:12][C:13]([F:17])([F:16])[CH2:14][N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3]

Participants

4

Reactant 2

HCID 7054IsatinHCID 677091,1,1-Trifluoro-2-iodoethane

Product 1

HCID 19600971HCID 19600971, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Sodium hydride (8.65 g of a 60% oil dispersion, 0.22 mol) was washed with hexane and suspended in hexamethylphosphoramide (200 mL). Isatin (29.4 g, 0.20 mol)) was added carefully. After the gas evolution subsided, 2,2,2-trifluoroethyl iodide (46.2 g, 0.22 mol) was added and the mixture was heated to 55° C. for 4 hours. The solution was cooled, diluted with water (1 L), and the precipitate was collected. The filtrate was acidified with 6 N HCl and a new precipitate formed and was collected. The combined solids were recrystallized from 95% ethanol. Yield 22.5 g (49%). mp 161-163° C.

Workup

  1. washSodium hydride (8.65 g of a 60% oil dispersion, 0.22 mol) was washed with hexane
  2. temperatureThe solution was cooled
  3. customthe precipitate was collected
  4. customa new precipitate formed
  5. customwas collected
  6. customThe combined solids were recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-75715625ac8c4c20a15efd9d6974e6d7
Source dataset
uspto-grants-1999_12
Patent number
US05998463

Reaction notes

Loading…