Triethylamine → HCID 118105755, compound

HRID 1496968Notes

Reaction equation

HRID 1496968 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[NH:7][CH3:8].C(N(CC)CC)C.[C:20](Cl)(=[O:23])[CH2:21][CH3:22].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([N:7]([CH3:8])[C:20](=[O:23])[CH2:21][CH3:22])[CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 2580415-chloro-N-methyl-2-nitroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 118105755HCID 118105755, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-chloro-N-methyl-2-nitroaniline (500 mg) was dissolved in methylene chloride anhydrous (9 mL), added with triethylamine (3 mL) and propionyl chloride (1 mL) and refluxed. Then, saturated sodium bicarbonate was added thereto and extracted with ethyl acetate. The extracted organic layer was washed with saturated sodium bicarbonate, dried with sodium sulfate, filtered and concentrated under reduced pressure. The concentrated filtrate was purified by column chromatography (silica gel, hexane/ethyl acetate) to obtain a target compound as a yellow solid.

Workup

  1. temperaturerefluxed
  2. extractionextracted with ethyl acetate
  3. washThe extracted organic layer was washed with saturated sodium bicarbonate
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrated filtrate was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c25fde5f062c47d4bc1da9b949c79b58
Source dataset
uspto-grants-2015_12
Patent number
US09199944B2

Reaction notes

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