4-Chloroaniline → HCID 14882892, compound

HRID 359099Notes

Reaction equation

HRID 359099 reaction equation
[C:1]([CH2:4][CH2:5][C:6]([N:8]([CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:7])(O)=[O:2].[Cl:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:30][C:31]1[CH:37]=[CH:36][C:34]([NH:35][C:1]([CH2:4][CH2:5][C:6]([N:8]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][CH:29]=2)[C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[O:7])=[O:2])=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 78124-ChloroanilineHCID 10868DicyclohexylcarbodiimideHCID 15086608HCID 15086608, compound

Product 1

HCID 14882892HCID 14882892, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 4-[3-[N-(3-carboxypropionyl)-N-(4-chlorophenyl)amino]propoxy]benzoate (1.6 g), p-chloroaniline (0.54 g), DCC (0.87 g) and 4-dimethylaminopyridine (47 mg) were dissolved in methylene chloride (40 ml), and the mixture was stirred at room temperature for 52 hours, and concentrated under reduced pressure. The residue was dissolved in a small amount of DMF, and filtered. To this filtrate were added water and ethyl acetate and it was separated into layers. The organic layer was washed with water 3 times and concentrated under reduced pressure. The oily product thus obtained was subjected to column chromatography on silica gel and eluted with a mixed solvent of chloroform/methanol [30:1 (v/v)], and then concentrated under reduced pressure. The residue was crushed in aqueous methanol and collected by filtration to give the subject product (1.70 g). mp. 128°-130° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in a small amount of DMF
  3. filtrationfiltered
  4. additionTo this filtrate were added water and ethyl acetate and it
  5. customwas separated into layers
  6. washThe organic layer was washed with water 3 times
  7. concentrationconcentrated under reduced pressure
  8. customThe oily product thus obtained
  9. washeluted with a mixed solvent of chloroform/methanol [30:1 (v/v)]
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was crushed in aqueous methanol
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e827be1ce1e84e02b09366bbbd7378d4
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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