Sodium Chloride → 184906-26-1

HRID 1737302Notes

Reaction equation

HRID 1737302 reaction equation
O[C:2]([CH3:14])([CH3:13])[CH2:3][C:4]1[C:5]([CH3:12])=[C:6]([OH:11])[C:7]([CH3:10])=[CH:8][CH:9]=1.[C-:15]#[N:16].[Na+].[Cl-]>O>[CH3:13][C:2]1([CH3:14])[CH2:3][C:4]2[C:9](=[CH:8][C:7]([CH3:10])=[C:6]([OH:11])[C:5]=2[CH3:12])[CH:15]=[N:16]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 5975CyanideHCID 10679357HCID 10679357, compound

Product 1

HCID 135480532184906-26-1

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tertiary alcohol 33 (12.5 g, 64.4 mmol) is subjected to the Ritter reaction according to general procedure B. The substrate is added to the acid/cyanide mixture (at rt) over a 2.5 h period, and the resulting red reaction mixture is stirred overnight at rt. Because of the high water solubility of the product, during the work-up the aqueous phase is saturated with NaCl, and extracted six times with EtOAc to obtain an acceptable recovery of material. The organic phase is dried (Na2SO4), filtered and concentrated. The residue is filtered through silica gel with 10:1 CH2Cl2 /MeOH, and the appropriate fractions are combined and diluted with hexane to produce 38 as yellow crystals, mp 220-234° C. (dec.). A lower Rf product is also isolated. This product displays the same type of TLC behavior (blue fluorescence), and a very similar 1H NMR spectrum, and is thought to be a symmetrical dimer. Upon standing in solution, this product is slowly converted into 38, which then precipitates. Three crops of the yellow crystals are collected for a total yield of 6.8 g (52%). 1H NMR (CD3OD, 3.30 ppm) 7.76 (s, 1), 7.10 (s, 1), 4.93 (s, 1), 2.82 (s, 2), 2.10 (s, 3), 2.07 (s, 3), 1.33 (s, 6); 13C NMR (CD3OD, 49.05 ppm) 158.21, 136.17, 134.91, 127.55, 126.90, 54.34, 38.15, 27.25, 17.02, 11.39; MS (MW=203.3, CI/CH4, eE=70 eV) m/z 204 [(M+H)+, base peak)], 188, 177, 122.

Workup

  1. extractionextracted six times with EtOAc
  2. customto obtain an acceptable recovery of material
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe residue is filtered through silica gel with 10:1 CH2Cl2 /MeOH
  7. additiondiluted with hexane

Sources & evidence

ORD record
ord-4283f13ea3d94f47ae03b64793e2394a
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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