Nitrogen mustard hydrochloride → HCID 68707339, compound

HRID 645488Notes

Reaction equation

HRID 645488 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].Cl.[Cl:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18]Cl)[CH3:16].[OH-].[Na+]>C1COCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[ClH:12].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:9]#[N:10])[CH2:18][CH2:17][N:15]([CH3:16])[CH2:14][CH2:13]1

Participants

7

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 14798Sodium HydroxideHCID 67592Benzeneacetonitrile, 2-fluoro-

Product 1

HCID 68707339HCID 68707339, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-fluorophenyl)acetonitrile (15 mmol) in THF (20 mL) are successively added bis-(2-chloroethyl)methylamine hydrochloride (16 mmol), tetrabutylammonium hydrogensulfate (1.5 mmol), and 40% aq. NaOH (20 mL), then the mixture is refluxed for 5.5 h. The reaction mixture is cooled at room temperature, diluted with water, then extracted with THF. The organic extracts are washed with water (×2) and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is dissolved in ether, then HCl in 1,4-dioxane is added. The precipitate is collected by filtration to give the titled compound, which is directly used for the next reaction without further purification; 1H NMR (DMSO) δ: 2.43-2.60 (4H, m), 2.86 (3H, d), 3.20-3.28 (2H, m), 4.02-4.04 (2H, m), 7.31-7.40 (2H, m), 7.48-7.60 (2H, m), 11.16 (1H, br).

Workup

  1. temperaturethe mixture is refluxed for 5.5 h
  2. extractionextracted with THF
  3. washThe organic extracts are washed with water (×2) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue is dissolved in ether
  8. additionHCl in 1,4-dioxane is added
  9. filtrationThe precipitate is collected by filtration

Sources & evidence

ORD record
ord-d8ddb81b61b543aca80cf8259e772303
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

Loading…