Sodium hydride → 8-(2,4-Dimethylphenyl)-2-methyl-4-(1-propylbutyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 598067

반응식

HRID 598067 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[O:17][CH:16]([CH3:19])[C:15](=[O:20])[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.[H-].[Na+].Br[CH:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27]>CN(C)C=O.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[O:17][CH:16]([CH3:19])[C:15](=[O:20])[N:14]([CH:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[C:13]=2[CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 589385588-(2,4-Dimethylphenyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one

생성물 1

HCID 589386018-(2,4-Dimethylphenyl)-2-methyl-4-(1-propylbutyl)-2H-1,4-benzoxazin-3(4H)-one수율 45.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 8-(2,4-dimethylphenyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one (300 mg, 1.12 mmol) in N,N-dimethylformamide (5 ml) was added sodium hydride (43 mg, 1.68 mmol). After the mixture was stirred at 80° C. for 30 min, 4-bromoheptane (804 mg, 4.49 mmol) was added. The mixture was stirred at 80° C. for 18 h and diluted with water. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with 5% ethyl acetate/n-hexane to afford 186 mg (30%) of the title compound.

후처리

  1. stirringThe mixture was stirred at 80° C. for 18 h
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography
  7. washeluting with 5% ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-fda62b9899ae4111a274094088656f75
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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