2-Furancarboxylic acid → HCID 18915875, compound

HRID 1379610Notes

Reaction equation

HRID 1379610 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C1CCC(N=C=NC2CCCCC2)CC1.[N:24]1([CH2:30][C:31]2[CH:32]=[C:33]([CH:46]=[CH:47][CH:48]=2)[O:34][CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[CH2:40][S:41][CH2:42][CH2:43][NH2:44])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCl>[N:24]1([CH2:30][C:31]2[CH:32]=[C:33]([CH:46]=[CH:47][CH:48]=2)[O:34][CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[CH2:40][S:41][CH2:42][CH2:43][NH:44][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:8])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 69192-Furancarboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 18915889HCID 18915889, compound

Product 1

HCID 18915875HCID 18915875, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

There was dissolved 1.12 g of 2-furancarboxylic acid in 50 ml of dichloromethane and added 2.06 g (0.01 mol) of DCC under cooling with ice and the mixture was stirred for 30 minutes. Thereto was added 3.65 g (0.01 mol) of N-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-(2-aminoethylthio)acetamide and the mixture was stirred for 18 hours at room temperature. The precipitate was filtrated off, and the filtrate was washed with water and dried over Glauber's salt. Then the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give 1.2 g of the titled compound as crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 18 hours at room temperature
  3. filtrationThe precipitate was filtrated off
  4. washthe filtrate was washed with water
  5. dry with materialdried over Glauber's salt
  6. customThen the solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-1e2e8e6076c74d30ac2b06f3d22be64a
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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