Sodium amide → HCID 66848663、化合物

HRID 2176158ノート

反応式

HRID 2176158 の反応式
[NH2-].[Na+].Cl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.Br[CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:18][CH:19]=1>O1CCCC1>[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:14][C:15]2[N:16]=[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:18][CH:19]=2)[NH2:12])=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 24533Sodium amideHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 534214634-Bromomethyl-2-phenyl-oxazole

生成物 1

HCID 66848663HCID 66848663、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A flask containing tetrahydrofuran (2.0 mL) was charged with sodium amide (152 mg, 3.69 mmol; Aldrich) and chilled to 0° C. (4-Fluorophenyl)hydrazine hydrochloride (400 mg, 2.46 mmol; Aldrich) was added in portions. After 5 minutes, the solid had completely dissolved and the ice bath was removed. Stirring was continued for 1 hour, then the solution was chilled again in an ice bath and 4-(bromomethyl)-2-phenyloxazole (586 mg, 2.46 mmol; Anichem) was added dropwise. After 30 minutes, the ice bath was removed and the reaction was heated to 50° C. overnight. The mixture was diluted with water (5 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title product which was carried on without further purification: LC/MS (DCI/NH3) m/z 267 (M+H−NH3)+.

後処理

  1. additionwas added in portions
  2. dissolutionthe solid had completely dissolved
  3. customthe ice bath was removed
  4. waitwas continued for 1 hour
  5. temperaturethe solution was chilled again in an ice bath
  6. waitAfter 30 minutes
  7. customthe ice bath was removed
  8. additionThe mixture was diluted with water (5 mL)
  9. extractionextracted with dichloromethane (2×10 mL)
  10. dry with materialThe combined organic extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a7eaaf5f84414eec9e2f4e981112a5e4
出典データセット
uspto-grants-2015_06
特許番号
US09063126B2

反応ノート

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