Water → 2-Chloro-6-(2,4-difluoro-phenoxy)-quinazoline

HRID 272592

反応式

HRID 272592 の反応式
[Cl:1][C:2]1[N:11]=[C:10](N)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[F:21])[CH:8]=2)[N:3]=1.N(OC(C)(C)C)=O.O>C1COCC1>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[F:21])[CH:8]=2)[N:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 589051302-Chloro-6-(2,4-difluoro-phenoxy)-quinazolin-4-ylamine

生成物 1

HCID 589051372-Chloro-6-(2,4-difluoro-phenoxy)-quinazoline収率 44.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Compound (1G) (21 g, 0.07 mol) was dissolved in THF (200 mL) and the solution added dropwise to a solution of t-butyl nitrite (16.5 mL, 0.14 mol) in THF (100 mL). The mixture was heated to reflux for 4 h, and after cooling to room temperature, the reaction mixture was poured into water and extracted with EtOAc (2×100 mL). The combined organic layers were dried over sodium sulfate and evaporated in vacuo. The crude product was purified by chromatography (silica gel, hexane: EtOAc, 4:1) giving 9.05 g of 2-chloro-6-(2,4-difluoro-phenoxy)-quinazoline (1H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. extractionextracted with EtOAc (2×100 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe crude product was purified by chromatography (silica gel, hexane: EtOAc, 4:1)

出典と根拠

ORDレコード
ord-a11f365f54df4e5f90ccbf118752ef52
出典データセット
uspto-grants-2008_11
特許番号
US07456185B2

関連ノート

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