Sodium hydride → 4-[2-(4-(Phenoxy)phenyl)ethoxy]-5,6,7,8-tetrahydroquinazoline

HRID 342511

反応式

HRID 342511 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[C:22]1[C:31]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=2[N:25]=[CH:24][N:23]=1.[Cl-].[NH4+]>O1CCCC1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][O:16][C:22]2[C:31]3[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=3[N:25]=[CH:24][N:23]=2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27603454-Phenoxyphenethyl alcoholHCID 125829694-Chloro-5,6,7,8-tetrahydroquinazolineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 537211284-[2-(4-(Phenoxy)phenyl)ethoxy]-5,6,7,8-tetrahydroquinazoline収率 51.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3.8 g (17.8 mmol) of 2-[4-(phenoxy)phenyl]ethanol were added to a suspension of 700 mg (23.3 mmol) of sodium hydride (80% suspension in oil) in 50 ml of dry tetrahydrofuran, and the mixture was stirred at 50° C. until the evolution of hydrogen had ceased. The mixture was cooled to room temperature, and 3.0 g (17.8 mmol) of 4-chloro-5,6,7,8-tetrahydroquinazoline were added. The mixture was then heated for 5 hours at 40° C. The reaction mixture was poured into saturated ammonium chloride solution and subsequently extracted with diethyl ether. The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel using n-heptane/ethyl acetate (2:1). 3.2 g of 4-[2-(4-(phenoxy)phenyl)ethoxy]-5,6,7,8-tetrahydroquinazoline were obtained in the form of a viscous yellow oil.

後処理

  1. temperatureThe mixture was then heated for 5 hours at 40° C
  2. extractionsubsequently extracted with diethyl ether
  3. dry with materialThe combined organic phase was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-105aa480178d4490b1c732729646db55
出典データセット
uspto-grants-1999_01
特許番号
US05859020

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