Acetyl chloride → N-[(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methyl]acetamide

HRID 589070노트

반응식

HRID 589070 반응식
[C:1](Cl)(=[O:3])[CH3:2].[N+:5]([C:8]1[C:13]2[NH:14][C:15]([CH2:24][NH2:25])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:16][O:17][C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-:7])=[O:6]>C(Cl)Cl.C(N(CC)C(C)C)(C)C>[N+:5]([C:8]1[C:13]2[NH:14][C:15]([CH2:24][NH:25][C:1](=[O:3])[CH3:2])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:16][O:17][C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-:7])=[O:6]

참가 물질

5

반응물 2

HCID 6367Acetyl chlorideHCID 904100791-(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methanamine

생성물 1

HCID 90409716N-[(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methyl]acetamide수율 70%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 81531Diisopropylethylamine용매

실험 절차

Acetyl chloride (15 μL, 0.21 mmol) was added to a mixture of 1-(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methanamine (50 mg, 0.2 mmol) in methylene chloride (3 mL), N,N-diisopropylethylamine (60 μL) and was stirred at room temperature for 1 h. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude N-[(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methyl]acetamide (0.040 g. 70%). LCMS calculated for C16H17N4O4 (M+H)+: m/z=329.1. found: 329.0.

후처리

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-691234e4504544cd90ba224fc0519b63
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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