Sodium Cyanide → HCID 135407249, compound

HRID 1737304Notes

Reaction equation

HRID 1737304 reaction equation
[C-:1]#N.[Na+].[CH3:4][C:5]1([CH3:18])[CH2:14][C:13]2[C:8](=[CH:9][C:10]([CH3:17])=[C:11]([OH:16])[C:12]=2[CH3:15])[CH:7]=[N:6]1>>[CH3:18][C:5]1([CH3:4])[N:6]=[CH:7][C:8]2[CH:9]=[C:10]([CH3:17])[C:11]([OH:16])=[C:12]([CH3:15])[C:13]=2[CH2:1][CH2:14]1

Participants

3

Reactant 2

HCID 8929Sodium CyanideHCID 135480532184906-26-1

Product 1

HCID 135407249HCID 135407249, compoundYield 8%

Procedure

The product from the previous reaction (4.9 g, 24 mmol) is treated with NaCN as described above for compound 38. The resulting crude, cyclized imine is purified by FC (19:1 CH2Cl2/MeOH, then 9:1 CH2Cl2 /MeOH) to afford a dark orange semi-solid (370 mg, 8%). 1H NMR (CDCl3) 7.50 (s, 1), 7.00 (s, 1), 3.34 (br s, 1), 3.00-2.95 (m, 2), 2.18 (s, 3), 2.13 (s, 3), 2.00-1.95 (m, 2), 1.41 (s, 6); 13C NMR (CDCl3) 173.41, 156.30, 143.13, 141.14, 127.66, 125.74, 112.00, 57.81, 36.79, 28.50, 28.41, 16.73, 12.38; MS (MW=217.3, EI, eE=70 eV) m/z 217 (M+), 161 (base peak)

Workup

  1. customThe product from the previous reaction (4.9 g, 24 mmol)
  2. customThe resulting crude, cyclized imine is purified by FC (19:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-51a855f7c72b4bb6afe9f1b0d746cee0
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

Loading…