Dicyclohexylcarbodiimide → HCID 178505337, compound

HRID 1262997Notes

Reaction equation

HRID 1262997 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, compound

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 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-a779e3afe0024049a88cc65b1329ffd4
Source dataset
uspto-grants-1984_06
Patent number
US04454338

Reaction notes

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