Dicyclohexylcarbodiimide → HCID 178505337, compound

HRID 371430Notes

Reaction equation

HRID 371430 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH:6]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])[C:7]([NH2:9])=[NH:8].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:34][S:35]([O:38][C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[C:44]([C:49](=[NH:51])[NH2:50])[CH:45]=2)[CH:40]=1)(=[O:37])=[O:36]>N1C=CC=CC=1>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[NH:6]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([O:15][C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[C:44]([C:49](=[NH:50])[NH2:51])[CH:45]=2)[CH:40]=1)=[O:14])[C:7]([NH2:9])=[NH:8]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonateHCID 178505353HCID 178505353, compound

Product 1

HCID 178505337HCID 178505337, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4.7 g of m-guanidinobenzoic acid methanesulfonate in 50 ml of anhydrous pyridine, was added 4.4 g of DCC. To the mixture, while being cooled in ice and stirred, was added 5.0 g of 6-amidino-2-naphthol methanesulfonate. After having been stirred for 24 hours, the reaction mixture was freed from the insolubles by filtration and the filtrate was mixed with ether. The oily substance which was formed was crystallized by adding ethyl acetate. Recrystallization from a mixture of methanol and ether gave 3.2 g of 6-amidino-2-naphthyl 3-guanidinobenzoate dimethanesulfonate.

Workup

  1. temperatureTo the mixture, while being cooled in ice
  2. stirringAfter having been stirred for 24 hours
  3. filtrationthe reaction mixture was freed from the insolubles by filtration
  4. additionthe filtrate was mixed with ether
  5. customThe oily substance which was formed
  6. customwas crystallized
  7. additionby adding ethyl acetate
  8. customRecrystallization
  9. additionfrom a mixture of methanol and ether

Sources & evidence

ORD record
ord-a0e5ea81d93840c6beace412d3a43f9e
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

Loading…