Methyl iodide → 6-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1045363노트

반응식

HRID 1045363 반응식
[C:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].CI.[C:17](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[N:11]([CH3:17])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 36419566-Acetyl-2H-1,4-benzoxazin-3(4H)-one

생성물 1

HCID 405391446-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-Acetyl-2H-benzo[b][1,4]oxazin-3(4H)-one (1 g, 5.23 mmol), methyl iodide (1.13 g, 7.84 mmol) and cesium carbonate (2.55 g, 7.84 mmol) were dissolved in DMF (2 mL). The reaction mixture was irradiated by microwave for 30 minutes at 100° C. The solvent was removed and extracted with dichloromethane. Purification by silica chromatography (ISCO) produced 6-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.9 g, 84%). 1H NMR (400 MHz, CDCl3): δ 7.63 (s, 1H), 7.60 (d, 1H), 7.01 (d, 1H), 4.70 (s, 2H), 3.42 (s, 3H), 2.60 (s, 3H); MS (ESI) m/z: Calculated for C11H11NO3: 205.1. found: 206.1 (M+H)+.

후처리

  1. customThe reaction mixture was irradiated by microwave for 30 minutes at 100° C
  2. customThe solvent was removed
  3. extractionextracted with dichloromethane
  4. customPurification by silica chromatography (ISCO)

출처 및 근거

ORD 기록
ord-7ab2d9a2963343aabcc2a81190f2ca72
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569282B2

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