Sodium Cyanide → HCID 10630879, compound

HRID 1737299Notes

Reaction equation

HRID 1737299 reaction equation
[CH3:1][C:2](O)([CH3:9])[CH2:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.[C-:11]#[N:12].[Na+]>CCCCCC.CCOC(C)=O>[CH3:1][C:2]1([CH3:9])[N:12]=[CH:11][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 10749436HCID 10749436, compound

Product 1

HCID 10630879HCID 10630879, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Treatment of the alcohol 25 from the previous reaction (15.9 g, 102 mmol) with NaCN according to general procedure B gives the cyclized imine directly as a dark liquid after FC (3:1 hexane/EtOAc). Yield: 4.15 g (25%). 1H NMR (CDCl3) 8.17(s,1), 7.36(d,1, J=4.8), 6.88(d,1,J=4.8), 2.75(s,2), 1.28(s,6); 13C NMR (CDCl3) 153.96, 141.02, 131.45, 125.79, 124.39, 56.24, 35.65, 28.03; MS(MW=165.3, EI, eE=70eV) m/z 165 (M+, base peak), 150, 138, 124, 123, 97, 86, 77, 69, 58, 45.

Sources & evidence

ORD record
ord-2aad915a68c046ed857124966f2ce4fc
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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