Triethylamine → N-(5-Methylisoxaz-3-oyl)-3-Nitrobenzylamine

HRID 840584Notes

Reaction equation

HRID 840584 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][NH2:8])([O-:3])=[O:2].[CH3:12][C:13]1[O:17][N:16]=[C:15]([C:18](Cl)=[O:19])[CH:14]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:12][C:13]1[O:17][N:16]=[C:15]([C:18]([NH:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:19])[CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1227223-NitrobenzylamineHCID 27368945-Methylisoxazole-3-carbonyl chloride

Product 1

HCID 47450419N-(5-Methylisoxaz-3-oyl)-3-NitrobenzylamineYield 79.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 500 mg (2.65 mmol) of 3-nitrobenzylamine in 20 mL of dichloromethane was stirred at room temperature as 463 mg (3.18 mmol) of 5-methyl-3-isoxazoyl chloride was added. To this solution was added 0.92 mL (6.62 mmol) of triethylamine. The reaction was stirred an additional 1 hour at room temperature, diluted with 75 mL of ethyl acetate and the organic phase washed with 1N aqueous hydrochloric acid (twice), water (twice) and saturated aqueous sodium bicarbonate (thrice). The resulting organic solution was dried over sodium sulfate, filtered, and concentrated to give 550 mg (79%) of the title compound as a yellow solid. MS(FD) m/z 261 (M+).

Workup

  1. additionwas added
  2. washthe organic phase washed with 1N aqueous hydrochloric acid (twice), water (twice) and saturated aqueous sodium bicarbonate (thrice)
  3. dry with materialThe resulting organic solution was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c2dd569eee14170abbdb74e94b79eec
Source dataset
uspto-grants-2002_04
Patent number
US06369070B1

Reaction notes

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