Water → HCID 1551584, compound

HRID 2210935Notes

Reaction equation

HRID 2210935 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14]/[CH:15]=[CH:16]/[CH2:17]Br.[OH2:19]>CN(C=O)C>[C:1]1(=[O:11])[N:5]([CH2:14]/[CH:15]=[CH:16]/[CH2:17][N:5]2[C:1](=[O:19])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

5

Reactant 3

HCID 962WaterHCID 641245trans-1,4-Dibromo-2-buteneHCID 24194345Phthalimide potassium salt

Product 1

HCID 1551584HCID 1551584, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium phthalimide (20 g, 108 mmol) was added in portions over 2 h to a stirred solution of (E)-1,4-dibromobut-2-ene (10.7 g, 50 mmol ) in DMF (100 ml) at room temperature. The mixture was stirred for a further 3 d at this temperature, then poured into water (100 ml), and the mixture was extracted with dichloromethane (5×100 ml). The organic extracts were dried, filtered and concentrated in vacuo to leave DMF (ca. 30 ml), and a white solid, which was filtered off and washed with ether (3×10 ml) to give (E)-1,4-diphthalimidobut-2-ene (15.75 g, 91%). δH (90 MHz, CDCl3) 4.28 (4H, d), 5.92 (2H, m), and 7.79 (4H, m).

Workup

  1. extractionthe mixture was extracted with dichloromethane (5×100 ml)
  2. customThe organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto leave DMF (ca. 30 ml)
  6. filtrationa white solid, which was filtered off
  7. washwashed with ether (3×10 ml)

Sources & evidence

ORD record
ord-053d7b0566fd42eca16541ee6e7a090e
Source dataset
uspto-grants-1995_10
Patent number
US05461079

Reaction notes

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