N,N-Dimethylaniline → N-(4-Dimethylamino-phenyl)-oxalamic acid ethyl ester

HRID 2093056Notes

Reaction equation

HRID 2093056 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:10]1C=CC=CC=1.[C:16](Cl)(=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>ClCCl>[CH2:20]([O:19][C:17](=[O:18])[C:16]([NH:10][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:9])[CH3:1])=[CH:4][CH:5]=1)=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 1049PyridineHCID 20884Ethoxalyl chloride

Product 1

HCID 595794N-(4-Dimethylamino-phenyl)-oxalamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N, dimethyl aniline (5.3 mmole) was dissolved in dichloromethane (20 ml). To this solution was added, pyridine (0.86 ml) and stirred at 0° C. Ethyl chlorooxalate (5.6 mmole) dissolved in dichloromethane (5 ml) was added slowly at 0° C. The reaction mixture was stirred at room temperature for 1 h, concentrated to dryness diluted with water, extracted with dichloromethane, washed with saturated brine and dried oven Na2SO4. Concentrate to gave the N-(4-Dimethylamino-phenyl)-oxalamic acid ethyl ester, which was used for the next step.

Workup

  1. additionTo this solution was added
  2. additionwas added slowly at 0° C
  3. concentrationconcentrated to dryness
  4. additiondiluted with water
  5. extractionextracted with dichloromethane
  6. washwashed with saturated brine
  7. dry with materialdried oven Na2SO4
  8. concentrationConcentrate

Sources & evidence

ORD record
ord-65ca07da87a34146aa58551fb17708c1
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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