4-Aminophenol → 4-(4-Aminophenoxy)-4'-phenylethynylbenzophenone

HRID 35990

反応式

HRID 35990 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]1([C:15]#[C:16][C:17]2[CH:31]=[CH:30][C:20]([C:21]([C:23]3[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=3)=[O:22])=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.CC(N(C)C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:26]2[CH:27]=[CH:28][C:23]([C:21]([C:20]3[CH:30]=[CH:31][C:17]([C:16]#[C:15][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:18][CH:19]=3)=[O:22])=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 4034-AminophenolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 40956574-Fluoro-4'-(phenylethynyl)benzophenone

生成物 1

HCID 233528134-(4-Aminophenoxy)-4'-phenylethynylbenzophenone収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

In a 250 mL flask equipped with nitrogen inlet, overhead stirring assembly, Dean-Stark trap, and reflux condenser were placed 4-aminophenol (5.46 g, 0.05 mol), 4-phenylethynyl-4'-fluorobenzophenone (15.02 g, 0.05 mol), potassium carbonate (7.6 g, 0.055 mol), toluene (20 mL), and DMAc (45 mL). The mixture was heated to 150° C. for 2 h, then cooled to room temperature. The reaction mixture was poured into water and the resulting light yellow powder was collected by filtration. Recrystallization from toluene afforded the desired product in 85% yield: m.p. 151°-153° C. IR (KBr); 3382 and 3314 cm-1 (NH2); 3049, 1599, and 1509 cm-1 (aromatic C--H); 2217 cm-1 (C=C); and 1645 cm-1 (C=O): Mass Spec. m/e (relative intensity): M+, 389.4 (100); FW=389.44 g/mol.

後処理

  1. customIn a 250 mL flask equipped with nitrogen inlet
  2. temperatureDean-Stark trap, and reflux condenser
  3. temperaturecooled to room temperature
  4. filtrationthe resulting light yellow powder was collected by filtration
  5. customRecrystallization from toluene

出典と根拠

ORDレコード
ord-c9bf34767f6240c1b6e5fc3d71b4a948
出典データセット
uspto-grants-1995_05
特許番号
US05412066

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