Potassium Cyanide → HCID 21539321, compound

HRID 1076228Notes

Reaction equation

HRID 1076228 reaction equation
[CH2:1]1[C:6]2([C:15](=[S:16])[NH:14][C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1.[C-]#N.[K+].N12CCN(CC1)CC2>C1C=CC=CC=1>[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([NH:23][C:24]([N:14]2[C:15](=[S:16])[C:6]3([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5]3)[NH:7][C:8]32[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:25])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 9237DabcoHCID 693254-Methylphenyl isocyanateHCID 853997NSC515893

Product 1

HCID 21539321HCID 21539321, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.8 Parts of 7,14-diazadispiro[5.1.5.2]pentadecane-15-thione, 2.92 parts of p-tolyl isocyanate, 0.2 parts of potassium cyanide and a trace of 1,4-diazabicyclo[2.2.2]octane in 100 parts of dry benzene were heated at reflux for 24 hours. The solvent was then evaporated off in vacuo and the residue treated with excess water and allowed to stand for 24 hours. The solution was extracted with chloroform and the axtracts dried and evaporated in vacuo. The residue was crystallised from ethanol to yield 5.4 parts of 14-p-tolylcarbamoyl-7,14-diazadispiro[5.1.5.2]pentadecane-15-thione as a colourless solid of melting point 127° to 129°C. This material gave the following elemental analysis by weight:

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solvent was then evaporated off in vacuo
  3. additionthe residue treated with excess water
  4. extractionThe solution was extracted with chloroform
  5. customthe axtracts dried
  6. customevaporated in vacuo
  7. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-01e1def291bc435ea14a4c7daabde2c9
Source dataset
uspto-grants-1976_05
Patent number
US03956310

Reaction notes

Loading…