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

HRID 589070Notes

Reaction equation

HRID 589070 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-691234e4504544cd90ba224fc0519b63
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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