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

HRID 27962

Reaction equation

HRID 27962 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-42984094acad406fb3c8f2df499fdace
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Linked notes

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