Ammonia → 5-Iodo-2-pyrrolidin-1-ylmethyl-benzoxazole

HRID 1916762Notes

Reaction equation

HRID 1916762 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:7][C:6]=2[CH:16]=1.[Na+].[I-:18].CNCCNC.N>O.[Cu]I.O1CCOCC1>[I:18][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:7][C:6]=2[CH:16]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 673655735-Bromo-2-pyrrolidin-1-ylmethyl-benzoxazole

Product 1

HCID 690723805-Iodo-2-pyrrolidin-1-ylmethyl-benzoxazole

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

71 mg (0.36 mmol) CuI, 1 g (3.55 mmol) 5-bromo-2-pyrrolidin-1-ylmethyl-benzoxazole and 1.07 g (7.15 mmol) NaI are successively placed in a flask in an argon atmosphere. Then 0.08 mL (0.73 mmol) N,N′-dimethylethylenediamine and 3.5 mL 1,4-dioxane are added and the reaction mixture is refluxed for 14 h. The reaction mixture is then combined with 20 mL concentrated ammonia solution at RT, diluted with 100 mL water and extracted with DCM. The organic phase is extracted three times with water and dried over Na2SO4.

Workup

  1. temperaturethe reaction mixture is refluxed for 14 h
  2. extractionextracted with DCM
  3. extractionThe organic phase is extracted three times with water
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-371121d5ca4b425d830d72f555e13005
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…