Bis(2-chloroethyl) ether → HCID 58382401, compound

HRID 1628043Notes

Reaction equation

HRID 1628043 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[CH2:10]([O:13][CH2:14][CH2:15]Cl)[CH2:11]Cl.[NH4+].[Br-].[OH-].[Na+]>CCOC(C)=O>[I:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:15][CH2:14][O:13][CH2:10][CH2:11]2)=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 4

HCID 8115Bis(2-chloroethyl) etherHCID 14798Sodium HydroxideHCID 25514Ammonium BromideHCID 832214-Iodo-o-toluidine

Product 1

HCID 58382401HCID 58382401, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask was charged with 4-iodo-2-methylaniline (2.0 g, 8.6 mmol), 2,2′-dichloroethyl ether (2.45 g, 17.2 mmol), NH4Br (8.28 g, 25 mmol), and an aqueous NaOH solution (42 wt %, 4.10 g, 42.9 mmol). The mixture was refluxed overnight. The reaction mixture was cooled to rt and diluted with EtOAc (20 mL). The organic layer was separated, and the aqueous layer extracted with EtOAc (20 mL). The combined organic layers were washed with water (20 mL), dried over MgSO4 and concentrated under reduced pressure. The material was purified on silica gel eluting with 10:1 hexane/EtOAc to give 4-(4-iodo-2-methylphenyl)morpholine (1.3 g, 50%): 1H NMR (CDCl3, 400 MHz): 7.48 (d, J=8.4 Hz, 2H), 6.76 (s, 2H), 3.84-3.82 (m, 4H), 2.88-2.85 (m, 4H), 2.26 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with EtOAc (20 mL)
  4. washThe combined organic layers were washed with water (20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe material was purified on silica gel eluting with 10:1 hexane/EtOAc

Sources & evidence

ORD record
ord-87360940f76948d59ccf311874fe0867
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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