Acetonitrile → HCID 54038612, compound

HRID 1107969Notes

Reaction equation

HRID 1107969 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:29])[C:14]([CH2:26][CH2:27]Cl)=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1OCCOCCOCCOCCOCCOC1.C[C:49]#[N:50]>>[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:29])[C:14]([CH2:26][CH2:27][C:49]#[N:50])=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 2855718-Crown-6HCID 54109087HCID 54109087, compound

Product 1

HCID 54038612HCID 54038612, compound

Procedure

N-(1-Octyl-5-chloroethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (3.0 g) was dissolved in CH3CN (30 ml), and NaCH (3.7 g) and 18-crown-6 (0.1 g) were added, which was followed by refluxing for 17 hr under a nitrogen atmosphere. CH3CN was evaporated under reduced pressure, and water (100 ml) was added to the obtained residue. The mixture was extracted twice with AcOEt (100 ml). The AcOEt layer was washed with saturated brine (100 ml) and dried over anhydrous sodium sulfate, and AcOEt was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: AcOEt/benzene=1/10-1/5) to give 1.14 g of N-(1-octyl-5-cyanoethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Workup

  1. temperatureby refluxing for 17 hr under a nitrogen atmosphere
  2. customCH3CN was evaporated under reduced pressure, and water (100 ml)
  3. additionwas added to the obtained residue
  4. extractionThe mixture was extracted twice with AcOEt (100 ml)
  5. washThe AcOEt layer was washed with saturated brine (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate, and AcOEt
  7. customwas evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluent: AcOEt/benzene=1/10-1/5)

Sources & evidence

ORD record
ord-09f78a61ad744296ab7a2cd7b58f9065
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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