Dicyclohexylcarbodiimide → HCID 13645142, compound

HRID 365060Notes

Reaction equation

HRID 365060 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14]([OH:16])=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[CH:22]1([N:28]=[C:29]=[N:30]C2CCCCC2)[CH2:27][CH2:26][CH2:25]C[CH2:23]1.NC1C=CC=C(C)N=1>ClCCl>[CH3:23][C:22]1[N:28]=[C:29]([NH:30][C:14](=[O:16])[CH:13]([O:12][C:11]2[CH:10]=[CH:9][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:21][CH:20]=3)=[CH:19][CH:18]=2)[CH3:17])[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 157652-Amino-6-methylpyridineHCID 20036900HCID 20036900, compound

Product 1

HCID 13645142HCID 13645142, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 100 ml of dichloromethane solution containing 1.99 g of 2-[4-(4-cyanophenoxy)-phenoxy]-propionic acid, which was cooled with ice water, was added slowly 1,46 g of dicyclohexylcarbodiimide with stirring. After this mixture was stirred for 15 minutes, 0.76 g of 2-amino-6-methylpyridine was added thereinto with stirring. A temperature of reacting mixture was returned to room temperature with stirring. A precipitated solid was removed through filtration, and then the obtained solution was poured into 200 ml of chilled water. An organic layer was separated therefrom, and it was washed with dilute hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride in this order, from which the solvent was distilled away after drying. The residue was purified through a column-chromatography [silica gel, developed with benzene/ethyl acetate=10/1(V/V)] to give 1.53 g of the title compound having melting point of 109°-111° C.

Workup

  1. stirringAfter this mixture was stirred for 15 minutes
  2. stirringwith stirring
  3. customwas returned to room temperature
  4. stirringwith stirring
  5. customA precipitated solid was removed through filtration
  6. additionthe obtained solution was poured into 200 ml of chilled water
  7. customAn organic layer was separated
  8. washit was washed with dilute hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride in this order, from which the solvent
  9. distillationwas distilled away
  10. customafter drying
  11. customThe residue was purified through a column-chromatography [silica gel

Sources & evidence

ORD record
ord-14214ac255c14c79a26868364a842b76
Source dataset
uspto-grants-1986_08
Patent number
US04608081

Reaction notes

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