Aniline → Hexakis(4-aminophenoxy)cyclotriphosphazene

HRID 648365Notes

Reaction equation

HRID 648365 reaction equation
[N+:1]([C:4]1[CH:66]=[CH:65][C:7]([O:8][P:9]2([O:55][C:56]3[CH:61]=[CH:60][C:59]([N+:62]([O-])=O)=[CH:58][CH:57]=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]([O:45][C:46]3[CH:51]=[CH:50][C:49]([N+:52]([O-])=O)=[CH:48][CH:47]=3)([O:35][C:36]3[CH:41]=[CH:40][C:39]([N+:42]([O-])=O)=[CH:38][CH:37]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-])=O.NC1C=CC=CC=1.[H][H]>O=[Pt]=O.C1COCC1>[NH2:1][C:4]1[CH:66]=[CH:65][C:7]([O:8][P:9]2([O:55][C:56]3[CH:61]=[CH:60][C:59]([NH2:62])=[CH:58][CH:57]=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]([O:45][C:46]3[CH:51]=[CH:50][C:49]([NH2:52])=[CH:48][CH:47]=3)([O:35][C:36]3[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=3)[N:10]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 272994Hexakis(4-nitrophenoxy)cyclotriphosphazeneHCID 178418361HCID 178418361, compound

Product 1

HCID 13444036Hexakis(4-aminophenoxy)cyclotriphosphazene

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 1000-mL stirrer-equipped autoclave was charged with 40.0 g (0.041 mol) of hexakis(4-nitrophenoxy)cyclotriphosphazene (2), aniline (75 mL), and 0.1 g of PtO2 catalyst. The mixture was agitated vigorously under 50 psi of hydrogen pressure at 50° C. until no further pressure drop was recorded (~30 h). The reaction mixture was filtered and the filtrate was poured slowly into toluene (1000 mL). Impure 3 precipitated from solution. After filtration, the crude 3 was recrystallized from o-dichlorobenzene and from THF to yield 30 g (92%) of pure 3, mp 189°-190° C. A 31P NMR spectrum in THF showed a singlet at 11.2 ppm, which indicated complete conversion of NO2 to NH2 groups.

Workup

  1. customA 1000-mL stirrer-equipped autoclave
  2. custom(~30 h)
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate was poured slowly into toluene (1000 mL)
  5. customImpure 3 precipitated from solution
  6. filtrationAfter filtration
  7. customthe crude 3 was recrystallized from o-dichlorobenzene and from THF
  8. customto yield 30 g (92%) of pure 3, mp 189°-190° C

Sources & evidence

ORD record
ord-8967162e58ad42b898c740ed3a446ef0
Source dataset
uspto-grants-1983_10
Patent number
US04412066

Reaction notes

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