Dabco → HCID 21539297, compound

HRID 1076227Notes

Reaction equation

HRID 1076227 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.[CH3:17][N:18]=[C:19]=[O:20].N12CCN(CC1)CC2>C1C=CC=CC=1>[CH3:17][NH:18][C:19]([N:14]1[C:15](=[S:16])[C:6]2([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5]2)[NH:7][C:8]21[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:20]

Participants

5

Reactant 3

HCID 9237DabcoHCID 12228Methyl Isocyanate2×HCID 853997NSC515893

Product 1

HCID 21539297HCID 21539297, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.8 Parts of 7,14-diazadispiro[5.1.5.2]pentadecane-15-thione, 2.28 parts of methyl isocyanate and a trace of 1,4-diazabicyclo[2.2.2]octane in 100 parts of dry benzene were heated at reflux for 4 days. A further 2.28 parts of methyl isocyanate were added and the solution again heated at reflux for 16 hours. The solvent was then evaporated in vacuo and the residue was crystallised twice from ethyl acetate to give 14-methylcarbamoyl-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 4 days
  2. temperaturethe solution again heated
  3. temperatureat reflux for 16 hours
  4. customThe solvent was then evaporated in vacuo
  5. customthe residue was crystallised twice from ethyl acetate

Sources & evidence

ORD record
ord-ad25879a620b44bdb3012342bd2e4636
Source dataset
uspto-grants-1976_05
Patent number
US03956310

Reaction notes

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