Triethylamine → HCID 131731791, compound

HRID 2408765Notes

Reaction equation

HRID 2408765 reaction equation
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)#[N:3].[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=O.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[N:11][NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]#[N:3])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6430496-chlorohexanalHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 131731791HCID 131731791, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4-cyanophenylhydrazine HCl (3.44 g, 20.3 mM) and 6-chlorohexanal (2.5 g, 18.6 mM) in toluene (30 mL) was added triethylamine at 0° C. (2.82 mL, 20.3 mM). The mixture was allowed to stir for 2 hours at ambient temperature. The mixture was filtered and the resultant filter cake was washed with toluene. The combined filtrate was concentrated under vacuum to give 4.92 g of a crude product, which was purified using conventional methods to yield 4.16 g (89.6%) of 4-(2-(6-chlorohexylidene)hydrazinyl)benzonitrile as a mixture of cis:trans isomers (ratio 5:1). NMR (400 MHZ, CDCl3): 7.6-6.6 (6H, (4H, dd-aromatic; 1H (m)-NH, 1H (t)-N═CH-t)), 3.57 (2H (t), CH2Cl), 2.2-2.4 (2H (m), ═CH—CH2), 1.75-1.90 (2H (m), CH2Cl—CH2), 1.49-1.65 (4H (m), CH2—CH2); m/z: 250 [M+H]+, calcd for [C13H16ClN3+H]+ 250.10.

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe resultant filter cake
  3. washwas washed with toluene
  4. concentrationThe combined filtrate was concentrated under vacuum
  5. customto give 4.92 g of a crude product, which
  6. customwas purified

Sources & evidence

ORD record
ord-cca9c16f089741d69cbe2208c15d1365
Source dataset
uspto-grants-2014_08
Patent number
US08815870B2

Reaction notes

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