Phenyl isocyanate → HCID 86733407, compound

HRID 1076217Notes

Reaction equation

HRID 1076217 reaction equation
[CH2:1]1[C:6]2([C:15](=[O: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([N:23]=[C:24]=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N12CCN(CC1)CC2>C1C=CC=CC=1>[C:17]1([NH:23][C:24]([N:14]2[C:15](=[O: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:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 9237DabcoHCID 965547,14-Diazadispiro(5.1.5.2)pentadecan-15-one

Product 1

HCID 86733407HCID 86733407, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.55 Parts of 7,14-diazadispiro[5.1.5.2]pentadecan-15-one, 2.97 parts of phenyl isocyanate and a trace of 1,4-diazabicyclo[2.2.2]octane in 100 parts of dry benzene were stirred and heated at reflux for 36 hours. After removal of the benzene by distillation under reduced pressure the residue was crystallised from petroleum ether of boiling range 60-80°C to give 4.50 parts of 14-phenylcarbamoyl-7,14-diazadispiro[5.1.5.2]pentadecan-15-one having a melting point of 129° to 130°C and the following elemental analysis by weight:

Workup

  1. temperatureheated
  2. temperatureat reflux for 36 hours
  3. customAfter removal of the benzene
  4. distillationby distillation under reduced pressure the residue
  5. customwas crystallised from petroleum ether of boiling range 60-80°C

Sources & evidence

ORD record
ord-b34a2e5f45fc47489cd3af2f64e8c0d5
Source dataset
uspto-grants-1976_05
Patent number
US03956310

Reaction notes

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