Dimethylamine → HCID 21473553, compound

HRID 2294136Notes

Reaction equation

HRID 2294136 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C(Cl)=O.[CH3:20][NH:21][CH3:22].[OH-].[Na+]>C(Cl)Cl.O1CCOCC1.O>[CH3:20][N:21]([CH3:22])[C:7](=[O:8])[C:6]1[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 183715-Methyl-2-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 21473553HCID 21473553, compoundYield 95.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-methyl-2-nitrobenzoic acid (10 g, 55.2 mmol) and oxalyl chloride (6 mL, 68.8 mmol) in 100 mL of methylene chloride was stirred under argon at room temperature for 2 hours. The mixture was concentrated and the residue was co-evaporated twice with toluene. The residue was dissolved in 60 mL of dioxane and the solution was added dropwise to a mixture of aqueous dimethylamine (8.2 g, 40% w/w, 72.7 mmol) and sodium hydroxide (2.2 g, 55 mmol) in 20 mL of dioxane at 0° C. The mixture was stirred at room temperature for 1 hour and then poured into water. The mixture was extracted with ethyl acetate (2×150 mL), dried (Na2SO4), filtered and concentrated to give N,N,5-trimethyl-2-nitrobenzamide (11 g, 52.8 mmol).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in 60 mL of dioxane
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. extractionThe mixture was extracted with ethyl acetate (2×150 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ec0b54d5cda246359004f35953e8e89e
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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