2,3-Dichloroaniline → HCID 21829908, compound

HRID 1600543Notes

Reaction equation

HRID 1600543 reaction equation
CN(C1C=CC=CN=1)C.Cl.CN(CCCN=C=NCC)C.[CH2:22]([N:24]1[CH:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:27](=[O:35])[N:26]([C:36]([CH3:41])([CH3:40])[C:37]([OH:39])=O)[CH2:25]1)[CH3:23].[Cl:42][C:43]1[C:49]([Cl:50])=[CH:48][CH:47]=[CH:46][C:44]=1[NH2:45]>ClCCl.O>[Cl:42][C:43]1[C:49]([Cl:50])=[CH:48][CH:47]=[CH:46][C:44]=1[NH:45][C:37](=[O:39])[C:36]([N:26]1[C:27](=[O:35])[CH:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:24]([CH2:22][CH3:23])[CH2:25]1)([CH3:41])[CH3:40]

Participants

7

Reactant 4

HCID 118442,3-DichloroanilineHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21829907HCID 21829907, compound

Product 1

HCID 21829908HCID 21829908, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Dimethylaminopyridine (50 mg) and dimethylaminopropylethylcarbodiimide hydrochloride (0.5 g) were added to a solution of 2-(1-ethyl-5-phenylimidazolidin-4-on-3-yl)isobutyric acid (0.6 g) prepared according to Example 8 in dichloromethane (15 mL) at 0° C. After stirring for 15 minutes at 0° C. to room temperature, 2,3-dichloroaniline (0.4 g) was added and the mixture was stirred overnight at room temperature. The reaction solution was poured into water whose pH was 2, and the mixture was extracted with chloroform. The organic layer was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the resulting crude product was purified by thin-layer chromatography (silica gel, ethyl acetate/n-hexane=2/3) to give 0.2 g of the title compound.

Workup

  1. customprepared
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe resulting crude product was purified by thin-layer chromatography (silica gel, ethyl acetate/n-hexane=2/3)

Sources & evidence

ORD record
ord-928ed02bbb3d406daf23837a5df88060
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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