Hexane → Tris(4-aminophenoxy)-tris(phenoxy)cyclotriphosphazene

HRID 465166Notes

Reaction equation

HRID 465166 reaction equation
[N+:1]([C:4]1[CH:57]=[CH:56][C:7]([O:8][P:9]2([O:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:14]=[P:13]([O:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=[P:11]([O:39][C:40]3[CH:45]=[CH:44][C:43]([N+:46]([O-])=O)=[CH:42][CH:41]=3)([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H].CCCCCC>NC1C=CC=CC=1.[Pt]=O>[NH2:1][C:4]1[CH:57]=[CH:56][C:7]([O:8][P:9]2([O:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:14]=[P:13]([O:22][C:23]3[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=3)([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=[P:11]([O:39][C:40]3[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=3)([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:10]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 14274513Tri(4-nitrophenoxy)tri(phenoxy)cyclotriphosphazeneHCID 178418361HCID 178418361, compound

Product 1

HCID 14274514Tris(4-aminophenoxy)-tris(phenoxy)cyclotriphosphazeneYield 70.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6115AnilineSolvent

Conditions

Temperature
50 °C

Procedure

A 250-ml heater-equipped autoclave pressure bottle was charged with a solution of 20 (16.0 g) in aniline (40 ml), containing catalyst platinum oxide (0.075 g). The mixture was agitated vigorously at 50° C. and 60 psi of hydrogen until no further pressure drop was observed (3-4 h). The reaction mixture was filtered and concentrated under reduced pressure to 10 ml and poured slowly into hexane. The hexane was decanted off. The light brown paste was then extracted with hot hexane until the maceration was difficult. The thick paste was cooled in ice to give a light-yellow solid, which recrystallized from o-dichlorobenzene to give a white solid. The solid was further boiled with n-hexane, filtered, and dried to yield 21 (10.0 g). DTA examination of this solid showed a melting point range from 115°-145° C.

Workup

  1. customA 250-ml heater-equipped autoclave pressure bottle
  2. custom(3-4 h)
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure to 10 ml
  5. additionpoured slowly into hexane
  6. customThe hexane was decanted off
  7. extractionThe light brown paste was then extracted with hot hexane until the maceration
  8. temperatureThe thick paste was cooled in ice
  9. customto give a light-yellow solid, which
  10. customrecrystallized from o-dichlorobenzene
  11. customto give a white solid
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-620a0e57dbf643daa69d9c61656c77c8
Source dataset
uspto-grants-1985_10
Patent number
US04550177

Reaction notes

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