Dicyclohexylcarbodiimide → HCID 13146252, compound

HRID 2413219Notes

Reaction equation

HRID 2413219 reaction equation
[CH:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:43])[NH2:42])[CH:37]=2)[CH:32]=1)(=O)=O>N1C=CC=CC=1>[CH:1]1([CH2:7][C:8]([O:10][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:42])[NH2:43])[CH:37]=3)[CH:32]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 21363Cyclohexaneacetic acidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146252HCID 13146252, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.5 g of cyclohexylacetic acid in 50 ml of anhydrous pyridine, while being cooled in ice and stirred, was added 4.4 g of DCC. After 30 minutes, 5.0 g of 6-amidino-2-naphthol methanesulfonate was added to the mixture, and stirred for 24 hours at room temperature. The insolubles were removed by filtration and ethyl ether was added to the filtrate. The precipitate was collected by filtration and recrystallized from a dimethylformaldehyde-ether mixture to obtain 3.0 g of a white powder of 6-amidino-2-naphthyl cyclohexylacetate methanesulfonate.

Workup

  1. stirringstirred for 24 hours at room temperature
  2. customThe insolubles were removed by filtration and ethyl ether
  3. additionwas added to the filtrate
  4. filtrationThe precipitate was collected by filtration
  5. customrecrystallized from a dimethylformaldehyde-ether mixture

Sources & evidence

ORD record
ord-659b828090ed4000a1cedcc99d54ff80
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

Loading…