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2-Chloro-4,6-diphenyl-1,3,5-triazine → 6-(4,6-Diphenyl-1,3,5-triazin-2-yl)-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

HRID 1627748
ノート
印刷プレビュー

反応式

HRID 1627748 の反応式
[CH3:1][C:2]1([CH3:25])[C:15]2[C:10]3=[C:11]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[N:9]3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=3)[CH:12]=[C:13](B(O)O)[CH:14]=2.Cl[C:27]1[N:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:30]=[C:29]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:39]1([C:29]2[N:30]=[C:31]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:32]=[C:27]([C:5]3[CH:4]=[C:3]4[C:8]5=[C:7]([C:23]6[CH:22]=[CH:21][CH:20]=[CH:19][C:24]=6[N:9]5[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=5[C:2]4([CH3:25])[CH3:1])[CH:6]=3)[N:28]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 673261988,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

生成物 1

HCID 680145136-(4,6-Diphenyl-1,3,5-triazin-2-yl)-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

試薬・触媒・溶媒 4

HCID 167845
palladium(II) acetate
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 312751,4-Dioxane溶媒

実験手順

36 g (110.0 mmol) of 8,8-dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid, 29.5 g (110.0 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 44.6 g (210.0 mmol) of tripotassium phosphate are suspended in 500 ml of toluene, 500 ml of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium (II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum, the purity is 99.9%. The yield is 46 g (89 mmol), corresponding to 83% of theory.

後処理

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from dichloromethane/isopropanol

出典と根拠

ORDレコード
ord-a6770a7d366e4c6b95e63f56fa609ed3
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785636B2

反応ノート

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