Hydrochloric Acid → HCID 67560689, compound

HRID 1683120Notes

Reaction equation

HRID 1683120 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[Cl:14][CH2:15][CH2:16][N:17]([CH2:25][CH2:26]Cl)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Br-].C([P+](CC)(CC)CC)CCCCCCCCCCCCCCC.Cl>CO.O>[ClH:14].[CH2:18]([N:17]1[CH2:25][CH2:26][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([C:9]#[N:10])[CH2:15][CH2:16]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochlorideHCID 21951238Triethyl(hexadecyl)phosphanium bromide

Product 1

HCID 67560689HCID 67560689, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluorophenyl-acetonitrile (5.89 g, 40 mmol), and aqueous sodium hydroxide solution (60 mL, 50% by weight) are combined and then N,N-Bis(2-chloroethyl)-N-benzylamine hydrochloride (11.28 g, 42 mmol) and hexadecyltriethyl phosphonium bromide (1.02 g, 2 mmol) were added. The reaction mixture was heated to 100° C. and stirred vigorously for 1 hour. The reaction mixture is cooled to ambient temperature and water was added. The diluted reaction mixture was acidified with 6M hydrochloric acid solution and extracted with diethyl ether. The aqueous layer is then made basic with solid potassium hydroxide and extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, filtered, and evaporated in vacuo to give a residue. The residue was added to a solution of hydrochloric acid in methanol and the solution was evaporated in vacuo to give a solid. The solid was recrystallized from methanol/ethyl acetate to the title compound: mp=263-264.

Workup

  1. temperatureThe reaction mixture is cooled to ambient temperature
  2. customThe diluted reaction mixture
  3. extractionextracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give a residue
  10. customthe solution was evaporated in vacuo
  11. customto give a solid
  12. customThe solid was recrystallized from methanol/ethyl acetate to the title compound

Sources & evidence

ORD record
ord-277cb69962b6420e81f5008c636614cd
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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