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

HRID 980001Notes

Reaction equation

HRID 980001 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-94c93b52e7b94d7bb40c548bdd3c1178
Source dataset
uspto-grants-1987_01
Patent number
US04634759

Reaction notes

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