2,3-Dimethylaniline → HCID 924918, compound

HRID 581182Notes

Reaction equation

HRID 581182 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([OH:10])=O)([O-:3])=[O:2].[CH3:15][C:16]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:15][C:16]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][C:8](=[O:10])[CH2:7][O:6][C:5]1[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 68932,3-DimethylanilineHCID 15883(2-Nitrophenoxy)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 924918HCID 924918, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(2-Nitrophenoxy)acetic acid S11 (5.28 g) and 2,3-dimethylaniline (3.25 g) were dissolved in dichloromethane (100 ml). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.17g) and 4-dimethylaminopyridine (3.93 g) were added to the solution, and the solution was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in dichloromethane. The resulting solution was washed successively with 1N HCl saturated aqueous sodium hydrogencarbonate solution and brine, then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, obtaining 7.7 g of the compound S12.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe resulting solution was washed successively with 1N HCl saturated aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-05dd3f56415d4b63ab2e9605b0748ff5
Source dataset
uspto-grants-1999_07
Patent number
US05919824

Reaction notes

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