Water → 7-Fluoro-6-nitro-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one

HRID 235582ノート

反応式

HRID 235582 の反応式
[H-].[Na+].[F:3][C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1.[CH2:18](Br)[C:19]#[CH:20].O>CN(C)C=O>[F:3][C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:7]2[N:8]([CH2:20][C:19]#[CH:18])[C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 137312977-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one

生成物 1

HCID 137312997-Fluoro-6-nitro-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one収率 69.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A suspension of sodium hydride (0.06 g) in N,N-dimethylformamide (3 ml) was cooled to 0° C. 7-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one (0.57 g) was added thereto at 0° to 5° C., and the resultant mixture was stirred for 30 minutes. Propargyl bromide (0.35 g) was added to the mixture, which was gradually heated to room temperature, and the reaction was continued for 6 hours. After addition of water, the resultant mixture was extracted with ethyl acetate, and the extract was washed with water, dried and concentrated. The residue was purified by silica gel thin layer chromatography using a mixture of ethyl acetate and n-hexane (1:1) as an eluent to give 7-fluoro-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.47 g). m.p., 109.1° C.

後処理

  1. temperaturewas gradually heated to room temperature
  2. extractionthe resultant mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel thin layer chromatography
  7. additiona mixture of ethyl acetate and n-hexane (1:1) as an eluent

出典と根拠

ORDレコード
ord-a43f51b33d7d492f8254adeb4f4be6ea
出典データセット
uspto-grants-1987_02
特許番号
US04640707

反応ノート

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