Dimethylformamide → 1-Ethyl-7-methoxy-5-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1504112ノート

反応式

HRID 1504112 の反応式
[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18](=[O:20])[CH2:17][C:16](=[O:21])[N:15]([CH3:22])[C:14]=2[CH:23]=1.[CH2:24](I)[CH3:25]>O>[CH2:24]([N:19]1[C:18](=[O:20])[CH2:17][C:16](=[O:21])[N:15]([CH3:22])[C:14]2[CH:23]=[C:10]([O:9][CH3:8])[CH:11]=[CH:12][C:13]1=2)[CH3:25]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 669610818-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

生成物 1

HCID 686748151-Ethyl-7-methoxy-5-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione収率 76.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (60% in oil, 44 mg) was suspended in of DMF (8 ml), and was cooled to 0° C. in an ice water bath. 8-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (220 mg) was added thereto at the same temperature, and the mixture was stirred at 0° C. for an hour. Ethyl iodide (187 mg) was added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction liquid, followed by extraction by ethyl acetate. The organic layer was dried over sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=4:1→1:1). The purified product was condensed to dryness to give the title compound (190.2 mg) as a yellow solid.

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction by ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=4:1→1:1)
  5. customcondensed to dryness

出典と根拠

ORDレコード
ord-520dd7c2c3254add87a77720bd94eefc
出典データセット
uspto-grants-2015_12
特許番号
US09212187B2

反応ノート

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