1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 53754840, compound

HRID 1262869Notes

Reaction equation

HRID 1262869 reaction equation
[Br:1][CH2:2][C:3](Br)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].N12CCCN=C1CCCCC2>CS(C)=O>[Br:1][CH:2]=[C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13320153HCID 13320153, compound

Product 1

HCID 53754840HCID 53754840, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1,2-dibromo-2-phenyl-3-phthalimidopropane (1.27 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.51 g) in dimethyl sulfoxide (DMSO, 50 ml) is heated at 90° for 16 hours. The solution is cooled, diluted with ice-water, and exhaustively extracted with ether. The orange oil (0.98 g) is chromatographed on silica gel (75 g) with 20% ethyl acetate in light petroleum as eluent to give a colorless mass which is crystallized from n-hexane/dichloromethane to give 1-bromo-2-phenyl-3-phthalimidopropene (0.66 g): colorless plates; m.p. 128°-129°;

Workup

  1. temperatureThe solution is cooled
  2. extractionexhaustively extracted with ether
  3. customThe orange oil (0.98 g) is chromatographed on silica gel (75 g) with 20% ethyl acetate in light petroleum as eluent
  4. customto give a colorless mass which
  5. customis crystallized from n-hexane/dichloromethane

Sources & evidence

ORD record
ord-fb0c24b8263541a491c7b63df7156dab
Source dataset
uspto-grants-1984_06
Patent number
US04454158

Reaction notes

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