Potassium cyanate → (9,10-Dihydro-9,10-methano-9-anthryl)acetonitrile

HRID 2198650

Reaction equation

HRID 2198650 reaction equation
S(O[CH2:12][C:13]12[CH2:27][CH:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=31)[C:19]1[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=1)(C1C=CC(C)=CC=1)(=O)=O.[O-][C:29]#[N:30].[K+]>CN(C)C=O.O>[CH:15]1[C:14]2[C:13]3([CH2:12][C:29]#[N:30])[CH2:27][CH:20]([C:21]4[C:26]3=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 11378442Potassium cyanateHCID 205199599-Tosyloxymethyl-9,10-dihydro-9,10-methanoanthracene

Product 1

HCID 13069087(9,10-Dihydro-9,10-methano-9-anthryl)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 9-tosyloxymethyl-9,10-dihydro-9,10-methanoanthracene (188 mg) and potassium cyanate (40 mg) in dimethylformamide (2 ml) was heated at 150° C. for 7 hours. The reaction mixture was diluted with water and extracted with benzene. The benzene extract was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give crude crystals of (9,10-dihydro-9,10-methano-9-anthryl)acetonitrile, which was recrystallized from isopropanol to give pure crystals. M.P. 130°-131° C.

Workup

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-94d72a7e56384f7589e3e478ca5d4832
Source dataset
uspto-grants-1982_11
Patent number
US04358620

Linked notes

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