Phenyl isocyanate → HCID 71105990, compound

HRID 1076226Notes

Reaction equation

HRID 1076226 reaction equation
[OH:1][N:2]1[C:11]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[NH:10][C:9](=[O:17])[C:3]21[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2.[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N12CCN(CC1)CC2>C1C=CC=CC=1>[OH:1][N:2]1[C:11]2([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[N:10]([C:25](=[O:26])[NH:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9](=[O:17])[C:3]21[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 9237DabcoHCID 22944372HCID 22944372, compound

Product 1

HCID 71105990HCID 71105990, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.6 Parts of 7-oxyl-7,14-diazadispiro[5.1.5.2]pentadecan-15-one (prepared from 7,14-diazadispiro[5.1.5.2]pentadecan-15-one by oxidation with hydrogen peroxide and sodium tungstate), 2.1 parts of phenyl isocyanate and a trace of 1,4-diazabicyclo[2.2.2]octane in 75 parts of dry benzene were heated at reflux for 18 hours. The solvent was evaporated in vacuo and the residue allowed to stand in 100 parts of water for 18 hours. The mixture was extracted thoroughly with chloroform and the extract washed with brine and dried over magnesium sulphate. Evaporation in vacuo afforded a solid material which was chromatographed on an alumina column to yield 7-oxyl-14-phenylcarbamoyl-7,14-diazadispiro[5.1.5.2]-pentadecan-15-one as pale red crystals of melting point 125° to 128°C. This material had the following elemental analysis by weight:

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent was evaporated in vacuo
  3. extractionThe mixture was extracted thoroughly with chloroform
  4. washthe extract washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customEvaporation in vacuo
  7. customafforded a solid material which
  8. customwas chromatographed on an alumina column

Sources & evidence

ORD record
ord-1318a5c25c384b43bfd3f4486d6436d0
Source dataset
uspto-grants-1976_05
Patent number
US03956310

Reaction notes

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