Trimethylsilyl cyanide → HCID 20225962, compound

HRID 1248775Notes

Reaction equation

HRID 1248775 reaction equation
Cl[CH:2]([O:13][CH2:14][C:15]([F:22])([N+:19]([O-:21])=[O:20])[N+:16]([O-:18])=[O:17])[O:3][CH2:4][C:5]([N+:10]([O-:12])=[O:11])([N+:7]([O-:9])=[O:8])[F:6].[C:23]([Si](C)(C)C)#[N:24]>ClC(Cl)C>[F:6][C:5]([N+:10]([O-:12])=[O:11])([N+:7]([O-:9])=[O:8])[CH2:4][O:3][CH:2]([O:13][CH2:14][C:15]([N+:19]([O-:21])=[O:20])([N+:16]([O-:18])=[O:17])[F:22])[C:23]#[N:24]

Participants

4

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 14205084HCID 14205084, compound

Product 1

HCID 20225962HCID 20225962, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of chloro bis(2-fluoro-2,2-dinitroethoxy)methane (2.45, 6.9 mmol) prepared in example 2 and cyanotrimethylsilane (0.77 g, 7.8 mmol) in 15 ml of dichloroethane was refluxed for 40 hours. NMR analysis showed consumption of the chloroformal and the presence of the cyanoformal together with a small amount of 2-fluoro-2,2-dinitroethyl formate. A 2.45 g residue from concentration of the reaction solution on a rotary evaporator was chromatographed on Silica Gel 60 (70-230 mesh, 25 g) with a 3:2 solvent mixture of hexanes/dichloromethane to give 1.51 g (63%) of bis(2-fluoro-2,2-dinitroethoxy)acetonitrile: mp 41°-2°; IR (film) 2260 (CN, weak) cm-1 ; 1H NMR (CDCl3): δ5.67 (s,l), 4.87 (d, 4, J=16 Hz); mass spectrum (CI, CH4), m/z (rel intensity): 386 (M+41, 3), 375 (M+30, 2), 319 (100 ), 92 (50).

Workup

  1. temperaturewas refluxed for 40 hours
  2. customconsumption of the chloroformal
  3. customA 2.45 g residue from concentration of the reaction solution on a rotary evaporator
  4. customwas chromatographed on Silica Gel 60 (70-230 mesh, 25 g) with a 3:2 solvent mixture of hexanes/dichloromethane

Sources & evidence

ORD record
ord-4c59c383707c43769d08fd7af13ff717
Source dataset
uspto-grants-1986_12
Patent number
USH0000181

Reaction notes

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