Hydrochloric Acid → HCID 59498061, compound

HRID 2061029Notes

Reaction equation

HRID 2061029 reaction equation
Br[C:2]([CH3:20])([CH2:18][Br:19])[C:3](=[N:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1CCN2C(=NCCC2)CC1.Cl>C1COCC1>[Br:19][CH:18]=[C:2]([CH3:20])[C:3](=[N:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59498159HCID 59498159, compound

Product 1

HCID 59498061HCID 59498061, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.83 g (4.59 mmol) of phenyl 2,3-dibromo-2-methyl-N-phenylpropanimidate in 10 ml of THF was added 770 mg (5.05 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene and stirred at room temperature for 2 hours. To the mixture was added 1N HCl and extracted with tert-butyl methyl ether. The combined organic layer was washed sequentially with a saturated aqueous NaHCO3 solution and a saturated NaCl solution, dried over anhydrous MgSO4, and then concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 1.26 g of phenyl 3-bromo-2-methyl-N-phenyl-2-propenimidate.

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. washThe combined organic layer was washed sequentially with a saturated aqueous NaHCO3 solution
  3. dry with materiala saturated NaCl solution, dried over anhydrous MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-2fb24d1fe59245f5a551ff5cde42e328
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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