Formaldehyde → N,N'-bis[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]hexahydropyrimidine

HRID 1941255Notes

Reaction equation

HRID 1941255 reaction equation
[O:1]=[C:2]1[C:11]2[C:6]3[C:7](=[CH:16][CH:17]=[CH:18][C:5]=3[C:4](=[O:19])[N:3]1[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][N:29]1[C:38](=[O:39])[C:37]3[CH:40]=[CH:41][CH:42]=[C:35]4[C:36]=3[C:31](=[C:32]3[CH:46]=[CH:45][CH:44]=[CH:43][C:33]3=[CH:34]4)[C:30]1=[O:47])[CH:8]=[C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]1=2.[CH2:48]=O>C(O)C>[O:47]=[C:30]1[C:31]2[C:36]3[C:35](=[CH:42][CH:41]=[CH:40][C:37]=3[C:38](=[O:39])[N:29]1[CH2:28][CH2:27][N:26]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:21][CH2:20][N:3]3[C:4](=[O:19])[C:5]4[CH:18]=[CH:17][CH:16]=[C:7]5[C:6]=4[C:11](=[C:10]4[CH:12]=[CH:13][CH:14]=[CH:15][C:9]4=[CH:8]5)[C:2]3=[O:1])[CH2:48]1)[CH:34]=[C:33]1[CH:43]=[CH:44][CH:45]=[CH:46][C:32]1=2

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 9830525HCID 9830525, compound

Product 1

HCID 10627814N,N'-bis[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]hexahydropyrimidineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.5 g (0.8 mmol) of N,N'-Bis[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]-1,3-propanediamine and 1 ml of 36% formaldehyde in 100 ml of ethanol was refluxed for 7 hours. The solid was filtered, washed, dried, and recrystallized from toluene. 0.3 g (58%) of N,N'-bis[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]hexahydropyrimidine were obtained. M.p. 222° C. (toluene).

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe solid was filtered
  3. washwashed
  4. customdried
  5. customrecrystallized from toluene

Sources & evidence

ORD record
ord-176e28769fa84d2f9143288edffd92bf
Source dataset
uspto-grants-1997_12
Patent number
US05703089

Reaction notes

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