Sodium hydride → 4-(6-Ethoxytetralin-2-yloxy)quinazoline

HRID 1385891ノート

反応式

HRID 1385891 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([OH:14])[CH2:8][CH2:7]2)[CH3:2].[H-].[Na+].Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][N:19]=1>C1COCC1.CCOCC>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([O:14][C:18]1[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=1)[CH2:8][CH2:7]2)[CH3:2]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 118302726-Ethoxytetralin-2-ol

生成物 1

HCID 110126414-(6-Ethoxytetralin-2-yloxy)quinazoline

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2.57 g (13.3 mmol) of 6-ethoxytetralin-2-ol in 5 ml of THF were added, with ice-cooling, to a suspension of 400 mg of NaH (80% pure, 13.3 mmol in 40 ml of THF). The mixture was subsequently refluxed for 1 hour and cooled to room temperature, and 2.0 g (12.2 mmol) of 4-chloroquinazoline were added. The mixture was refluxed for 24 hours and cooled and then diluted with ether and washed with saturated sodium hydrogen carbonate and saturated sodium chloride solution. After the organic phase had been dried and concentrated, the residue was chromatographed on silica gel using petroleum ether/ethyl acetate (9:1, 8:2). This gave 2.39 g (61% of theory) of colorless crystals (m.p.115-117° C.).

後処理

  1. temperatureThe mixture was subsequently refluxed for 1 hour
  2. temperatureThe mixture was refluxed for 24 hours
  3. temperaturecooled
  4. washwashed with saturated sodium hydrogen carbonate and saturated sodium chloride solution
  5. customAfter the organic phase had been dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-7b9e9785ddf64b9686c66a0c08697aac
出典データセット
uspto-grants-2001_07
特許番号
US06265398B1

反応ノート

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