N-bromobutanimide → HCID 18968849, compound

HRID 398824Notes

Reaction equation

HRID 398824 reaction equation
[CH:1]([Si:4]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[N:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1)([CH3:3])[CH3:2].BrN1[C:21](=O)[CH2:20][CH2:19]C1=O>O1CCCC1>[CH:13]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:10]([CH3:12])[CH3:11])[N:5]1[CH:9]=[CH:8][C:7]([Si:4]([CH:10]([CH3:12])[CH3:11])([CH:20]([CH3:21])[CH3:19])[CH:1]([CH3:3])[CH3:2])=[CH:6]1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 145136N-Triisopropylsilylpyrrole

Product 1

HCID 18968849HCID 18968849, compoundYield 137.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The product from step (a) (102.6 g) was dissolved in tetrahydrofuran (600 ml) and treated with N-bromosuccinimide (89 g) at -78° C. under nitrogen for 15 minutes. The reaction was allowed to come to ambient temperature over one hour, concentrated, diluted with hexane, filtered and the solvent removed. The residue was dissolved in tetrahydrofuran (600 ml), cooled to -78° C., and tert-butyl lithium in pentane (588 ml 1.7M) was added. After one hour elemental sulfur (16 g) was added and the mixture was stirred for one hour at ambient temperature. The reaction was cooled to -78° C. and triisopropyl silyl chloride (98 g) was added and the reaction was allowed to warm to room temperature. After 24 hrs the solvent was removed under reduced pressure and the residue in diethyl ether was washed with water, dried over sodium sulfate, filtered, concentrated and distilled at 160°-205° C. (0.2 mm) to give a colorless viscous oil (119.8 g). 1H NMR is consistent with proposed structure.

Workup

  1. concentrationconcentrated
  2. additiondiluted with hexane
  3. filtrationfiltered
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in tetrahydrofuran (600 ml)
  6. additiontert-butyl lithium in pentane (588 ml 1.7M) was added
  7. additionAfter one hour elemental sulfur (16 g) was added
  8. temperatureThe reaction was cooled to -78° C.
  9. additiontriisopropyl silyl chloride (98 g) was added
  10. temperatureto warm to room temperature
  11. customAfter 24 hrs the solvent was removed under reduced pressure
  12. washthe residue in diethyl ether was washed with water
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated
  16. distillationdistilled at 160°-205° C. (0.2 mm)

Sources & evidence

ORD record
ord-fd5e433b5c394f64ae7f3cbe8fee07fd
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Reaction notes

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