Acetic Anhydride → N-acetyl-4-ethynyl-3-nitrobenzamide

HRID 1844786Notes

Reaction equation

HRID 1844786 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])#[CH:2].[C:15](OC(=O)C)(=[O:17])[CH3:16]>C(O)(=O)C>[C:15]([NH:9][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[CH:2])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 569623664-Ethynyl-3-nitrobenzamide

Product 1

HCID 57331453N-acetyl-4-ethynyl-3-nitrobenzamideYield 22.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

4 g (0.021 mol) 4-Ethynyl-3-nitrobenzamide (Compound I-1), 30 ml (0.320 mol) acetic anhydride and 20 ml acetic acid were added into a reaction flask, stirred, and heated to 120° C. for 15 hours. After completion of the reaction monitored by TLC, the mixture was extracted with 300 ml ethyl acetate, and the organic layer was washed with water for three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness, separated by column chromatography to obtain N-acetyl-4-ethynyl-3-nitrobenzamide (Compound I-11), 1.1 g (0.0047 mol), yield 22.6%.

Workup

  1. extractionthe mixture was extracted with 300 ml ethyl acetate
  2. washthe organic layer was washed with water for three times
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated to dryness
  6. customseparated by column chromatography

Sources & evidence

ORD record
ord-7fd2ef2c5f17443797f467f183cc894c
Source dataset
uspto-grants-2015_02
Patent number
US08946478B2

Reaction notes

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