Sodium Cyanide → HCID 14011696, compound

HRID 845268Notes

Reaction equation

HRID 845268 reaction equation
[C-:1]#[N:2].[Na+].[CH3:4][C:5]1[NH:6][C:7]([CH3:31])=[C:8]([C:24]([O:26][CH2:27][CH2:28][CH2:29]Cl)=[O:25])[CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]>CS(C)=O>[CH3:4][C:5]1[NH:6][C:7]([CH3:31])=[C:8]([C:24]([O:26][CH2:27][CH2:28][CH2:29][C:1]#[N:2])=[O:25])[CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 20132470HCID 20132470, compound

Product 1

HCID 14011696HCID 14011696, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
120 °C

Procedure

0.55 g (11 mmol) of sodium cyanide in 15 ml of dimethylsulphoxide are added dropwise at a reaction temperature of 60° C. to a solution of 4.09 g (10 mmol) of 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(2-nitrophenyl)-5-(3-chloropropoxy)carbonyl-pyridine in 10 ml of dimethylsulphoxide. The reaction mixture is then stirred for 2.5 hours at 120° C. and is poured into 150 ml of ice water after it has cooled down. The mixture is extracted with 3×50 ml of ethyl acetate. After dehydration and concentration of the organic phases by evaporation under vacuum, 5.7 g of a brown oil are obtained. This oil is chromatographed on silica gel with dichloromethane/methanol (99:1). After concentration by evaporation under vacuum and recrystallisation of the residue from methanol, the main fraction yields 2.7 g (68%) of yellow crystals, melting point 48°-51° C.

Workup

  1. temperaturehas cooled down
  2. extractionThe mixture is extracted with 3×50 ml of ethyl acetate
  3. customAfter dehydration and concentration of the organic phases by evaporation under vacuum, 5.7 g of a brown oil
  4. customare obtained
  5. customThis oil is chromatographed on silica gel with dichloromethane/methanol (99:1)
  6. concentrationAfter concentration
  7. customby evaporation
  8. customunder vacuum and recrystallisation of the residue from methanol

Sources & evidence

ORD record
ord-6e54bc8944dd4623a60bbaf7433d2d36
Source dataset
uspto-grants-1988_07
Patent number
US04757080

Reaction notes

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