Butyl iodide → HCID 22599575, compound

HRID 1760113Notes

Reaction equation

HRID 1760113 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[O:13])[NH:5][CH2:4][C:3]1=[O:14].CC(C)([O-])C.[K+].I[CH2:22][CH2:23][CH2:24][CH3:25].C(OCC)(=O)C.CCCCCC>CN(C)C=O.C(Cl)Cl>[CH2:22]([N:5]1[C:6](=[O:13])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3](=[O:14])[CH2:4]1)[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 10962Butyl iodideHCID 35623871-Methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dioneHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22599575HCID 22599575, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 13 mmol of 3,4-dihydro-1-methyl-1H-1,4-benzodiazepin-2,5-dione (Tett. Lett. 1994, 50(30), 9051, incorporated herein by reference) in 30 mL dry dimethylformamide is treated, dropwise at 0° C. under nitrogen cover, with one equivalent of potassium-t-butoxide (Aldrich; 1.0 M in THF). After forty-five minutes at 0° C., iodobutane is introduced via syringe over several minutes. The reaction mixture is stirred at ambient temperature seventy-five minutes, diluted with methylene chloride, and then washed with water and saturated sodium chloride. The organic solution is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow oil. Flash column chromatography (silica gel; ethyl acetate/hexane (7/1) eluent) provides pure material as a colorless oil (90% yield).

Workup

  1. additionis treated, dropwise at 0° C. under nitrogen cover
  2. waitAfter forty-five minutes at 0° C.
  3. washwashed with water and saturated sodium chloride
  4. dry with materialThe organic solution is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-f62d4edd60d14c1f80b0eae0c7750451
Source dataset
uspto-grants-2005_01
Patent number
US06838455B2

Reaction notes

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