Dabco → Pentadecanal

HRID 1076218Notes

Reaction equation

HRID 1076218 reaction equation
[CH2:1]1[C:6]2([C:15](=[O:16])NC3(CCCCC3)N2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17](N=C=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]N=C=O.N12CCN(CC1)[CH2:31][CH2:30]2>C1C=CC=CC=1>[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:30][CH2:31][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:6][CH:15]=[O:16]

Participants

5

Reactant 3

HCID 9237DabcoHCID 13192Hexamethylene diisocyanateHCID 965547,14-Diazadispiro(5.1.5.2)pentadecan-15-one

Product 1

HCID 17697Pentadecanal

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.5 Parts of 7.14-diazadispiro[5.1.5.2]pentadecan-15-one, 2.1 parts of hexamethylene diisocyanate and a trace of 1,4-diazabicyclo[2.2.2]octane in 150 parts of dry benzene were refluxed for 48 hours. The solvent was removed in vacuo and the solid material stirred in 150 parts of water for 30 minutes. The solid was filtered and recrystallised from ethanol to give hexane-1',6'-bis[14-carbamoyl-7,14-diaza dispiro5.1.5.2]pentadecan-15-one] of melting point 164° to 165°C. This material gave the following elemental analysis by weight.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationThe solid was filtered
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-ebc9e2add1a24f0e9337d02b855f604e
Source dataset
uspto-grants-1976_05
Patent number
US03956310

Reaction notes

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