Sodium Cyanide → HCID 70623609, compound

HRID 372235Notes

Reaction equation

HRID 372235 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[C:16]3[CH2:25][N:24]4[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]4)[CH2:18][CH2:17]3)[C:4]=2[CH:3]=1.[C-:26]#[N:27].[Na+]>CN(C)C=O>[C:26]([C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[C:16]3[CH2:25][N:24]4[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]4)[CH2:18][CH2:17]3)[C:4]=2[CH:3]=1)#[N:27]

Participants

4

Reactant 2

HCID 8929Sodium Cyanide2×HCID 70624237HCID 70624237, compound

Product 1

HCID 70623609HCID 70623609, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 3.96 g. (0.01 mole) of 3-(2-bromothioxanthen-9-ylidene)quinolizidine, 2.70 g. (0.015 mole) of cuprous cyanide, 50 mg. of cupric sulfate, 50 mg. of sodium cyanide in 40 ml. of dimethylformamide is heated at reflux temperature for eighteen hours. The cooled reaction mixture is then poured into 200 ml. of 1 M sodium cyanide. The resulting mixture is extracted with ether. After being washed with an aqueous solution of sodium cyanide and water, the ether solution is dried over magnesium sulfate. The dried solution is concentrated. The residual liquid is chromatographed on an alumina column using ether as the eluate. Evaporation of the appropriate fractional eluant gives 3-(2-cyanothioxanthen-9-ylidene)quinolizidine. A solution of the product in ethanol is treated with a molar equivalent of fumaric acid. The resulting crystals are recrystallized from ethanol to give 3-(2-cyanothioxanthen-9-ylidene)quinolizidine fumarate.

Workup

  1. additionA stirred mixture of 3.96 g
  2. temperatureat reflux temperature for eighteen hours
  3. customThe cooled reaction mixture
  4. additionis then poured into 200 ml
  5. extractionThe resulting mixture is extracted with ether
  6. washAfter being washed with an aqueous solution of sodium cyanide and water
  7. dry with materialthe ether solution is dried over magnesium sulfate
  8. concentrationThe dried solution is concentrated
  9. customThe residual liquid is chromatographed on an alumina column
  10. customEvaporation of the appropriate fractional eluant

Sources & evidence

ORD record
ord-1412c7e3d4174bd7939de9f5bd404d7c
Source dataset
uspto-grants-1978_05
Patent number
US04089961

Reaction notes

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