Aniline → HCID 14274517, compound

HRID 1382474Notes

Reaction equation

HRID 1382474 reaction equation
[N+:1]([C:4]1[CH:58]=[CH:57][C:7]([O:8][P:9]2([O:47][C:48]3[CH:53]=[CH:52][C:51]([N+:54]([O-])=O)=[CH:50][CH:49]=3)[N:14]=[P:13]([O:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=3)([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[N:12]=[P:11]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-])=O.NC1C=CC=CC=1.[H][H]>[Pt]=O.C1CCCCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][P:9]2([O:47][C:48]3[CH:49]=[CH:50][C:51]([NH2:54])=[CH:52][CH:53]=3)[N:14]=[P:13]([O:25][C:26]3[CH:27]=[CH:28][C:29]([NH2:32])=[CH:30][CH:31]=3)([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[N:12]=[P:11]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:10]=2)=[CH:57][CH:58]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 14274516HCID 14274516, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14274517HCID 14274517, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8078CyclohexaneSolvent

Procedure

2,2,4,4-Tetra(p-nitrophenoxy)-6,6-diphenylcyclotriphosphazene (16.01 g, 0.021 moles), platinum oxide catalyst (0.09 g, 0.0004 moles), and 50 mls aniline are added to a 500 ml Fischer-Porter reaction vessel. The reaction is heated to 50° C. at 50-60 psi of hydrogen pressure for 65 hours. The reaction mixture is then cooled and concentrated to about 25 mls under vacuum. The concentrate is poured into 250 mls cyclohexane, and a brown coagulate forms. The solvent is decanted off and the residue is poured into hot cyclohexane and allowed to cool until stirring becomes difficult. The solvent is decanted off and the residue chilled for about 20 minutes. Recrystallization from o-dichlorobenzene yields a pale brown precipitate, which is boiled in cyclohexane for two hours. A solid is recovered (10.8 g, 78% yield). 31P NMR (THF), δ21.3(triplet), 10.1(doublet).

Workup

  1. temperatureThe reaction mixture is then cooled
  2. concentrationconcentrated to about 25 mls under vacuum
  3. additionThe concentrate is poured into 250 mls cyclohexane
  4. customThe solvent is decanted off
  5. additionthe residue is poured into hot cyclohexane
  6. temperatureto cool
  7. customThe solvent is decanted off
  8. temperaturethe residue chilled for about 20 minutes
  9. customRecrystallization from o-dichlorobenzene
  10. customyields a pale brown precipitate, which
  11. customA solid is recovered (10.8 g, 78% yield)

Sources & evidence

ORD record
ord-69d50acd736144b8ba6b9cf24e356667
Source dataset
uspto-grants-1989_02
Patent number
US04806607

Reaction notes

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