N,N-Dimethylaniline → HCID 22387845, compound

HRID 1699890Notes

Reaction equation

HRID 1699890 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22].CN(C)C1C=CC=CC=1.[C:32](Cl)(=[O:36])[C:33](Cl)=[O:34]>C1(C)C=CC=CC=1>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH2:14][N:13]1[C:3]2[C:2](=[CH:12][CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=2)[NH:1][C:33](=[O:34])[C:32]1=[O:36]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 65578Oxalyl chlorideHCID 22387919HCID 22387919, compound

Product 1

HCID 22387845HCID 22387845, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 4-amino3-(2,4-dichlorobenzylamino)benzoate (1.53 g) and dimethylaniline (0.71 g) in toluene was added oxalyl dichloride (0.51 ml). After stirring at room temperature for 1.5 hr, ice was added to the reaction mixture. The toluene layer was separated and washed with 6N hydrochloric acid. The toluene layer was concentrated, and the residue was washed with methyl t-butyl ether and dried to give the object compound (1.03 g) as white crystals.

Workup

  1. additionice was added to the reaction mixture
  2. customThe toluene layer was separated
  3. washwashed with 6N hydrochloric acid
  4. concentrationThe toluene layer was concentrated
  5. washthe residue was washed with methyl t-butyl ether
  6. customdried

Sources & evidence

ORD record
ord-49da3ad7f9c44a44b211661da169a8ea
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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