Bis(2-chloroethyl) ether → HCID 12510330, compound

HRID 2050218Notes

Reaction equation

HRID 2050218 reaction equation
[C:1]12([O:11][C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Li]CCCC.Cl[CH2:25][CH2:26][O:27][CH2:28][CH2:29]Cl>C1COCC1.CCCCCC>[C:1]12([O:11][C:12]3[CH:13]=[CH:14][C:15]([N:16]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:17][CH:18]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 72894774-(1-Adamantyloxy)anilineHCID 178418339Butyllithium2×

Product 1

HCID 12510330HCID 12510330, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent2×

Procedure

To 12.2 g (0.050 mole) of 4-(1-adamantyloxy)aniline dissolved in 200 ml of THF cooled in an ice bath was added dropwise with stirring 47 ml of a 1.07 M solution of n-BuLi in hexane. During the addition 100 ml of THF was added to the reaction mixture, and the mixture was stirred for one hour. 7.16 g (0.050 mole) of bis(2-chloroethyl)ether was added (as a solution in THF) and the mixture was refluxed for nineteen hours and allowed to cool. An additional 47 ml of the 1.07 M solution of n-BuLi in hexane was added dropwise with stirring to the reaction mixture cooled in an ice bath, and the mixture was stirred for one hour at room temperature and refluxed for twenty-three hours.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added dropwise
  3. additionwas added to the reaction mixture
  4. temperaturewas refluxed for nineteen hours
  5. temperatureto cool
  6. stirringwith stirring to the reaction mixture
  7. temperaturecooled in an ice bath
  8. stirringthe mixture was stirred for one hour at room temperature
  9. temperaturerefluxed for twenty-three hours

Sources & evidence

ORD record
ord-af799d9a88a84c16b1b03464ec30700a
Source dataset
uspto-grants-1980_04
Patent number
US04200588

Reaction notes

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