Triethylamine → HCID 22922595, compound

HRID 2258547Notes

Reaction equation

HRID 2258547 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[CH:15][C:10]=3[N:9]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:8]2=[O:25])=[C:4]([O:28][CH3:29])[CH:3]=1.Cl[CH2:31]/[CH:32]=[CH:33]\[CH2:34]Cl.C(N(CC)CC)C>CN(C=O)C>[CH:19]1([N:9]2[C:10]3[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[CH:13]=[CH:12][C:11]=3[N:7]([CH2:6][C:5]3[CH:26]=[CH:27][C:2]([N:1]4[CH:34]=[CH:33][CH:32]=[CH:31]4)=[CH:3][C:4]=3[O:28][CH3:29])[C:8]2=[O:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64321151,4-Dichloro-cis-2-buteneHCID 22922550HCID 22922550, compound

Product 1

HCID 22922595HCID 22922595, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1 g of the compound obtained in Example 6, 1 g of cis-1,4-dichloro-2-butene and 1 ml of triethylamine in 20 ml of DMF is heated at reflux for 1 hour 30 minutes under nitrogen atmosphere. After cooling, the reaction mixture is poured into a water/ice mixture, extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica, eluting with DCM. 0.5 g of the expected product is obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour 30 minutes under nitrogen atmosphere
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc
  5. washthe organic phase is washed with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated off under vacuum
  8. customThe residue is chromatographed on silica
  9. washeluting with DCM

Sources & evidence

ORD record
ord-dba2a0c685544285b56b1950320891f2
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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