Hydrochloric Acid → HCID 135754680, compound

HRID 1493019Notes

Reaction equation

HRID 1493019 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11]2[S:12][C:13](S(C)(=O)=O)=[N:14][N:15]=2)[CH:8]=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[OH:24])([CH3:4])[CH3:3].[C-:25]#[N:26].[Na+].Cl>CN(C)C=O>[CH3:23][C:20]([C:7]1[CH:8]=[C:9]([C:11]2[S:12][C:13]([C:25]#[N:26])=[N:14][N:15]=2)[CH:10]=[C:5]([C:2]([CH3:3])([CH3:4])[CH3:1])[C:6]=1[OH:24])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium Cyanide2×HCID 135786529HCID 135786529, compound

Product 1

HCID 135754680HCID 135754680, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 0.52 g (1.41 mmol) of methyl sulfone (Example 36) and 0.15 g (3.06 mmol, 2.17 equiv. ) of NaCN in 4 ml dimethylformamide is warmed at 65° C. for 25 hours. An additional portion of NaCN is added and the reaction is warmed at 75° C. for 16 hours and 85° C. for one hour. The reaction is poured onto 3N aqueous HCl and extracted with ethyl acetate (three times). The combined extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography (SiO2, 230-400 mesh, 15×4.5 cm, 15% ethyl acetate-hexane) gives 0.20 g of the nitrile. Recrystallization from cyclohexane gives 0.14 g (0.44 g theor., 31%) of the pure nitrile, mp 140°-140.5° C.

Workup

  1. extractionextracted with ethyl acetate (three times)
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73d4e5a591e44e3a89db1249f2b31745
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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