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

HRID 35990

반응식

HRID 35990 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 233528134-(4-Aminophenoxy)-4'-phenylethynylbenzophenone수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c9bf34767f6240c1b6e5fc3d71b4a948
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412066

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