Dicyclohexylcarbodiimide → HCID 178505336, compound

HRID 1263008Notes

Reaction equation

HRID 1263008 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH:6]([C:10]1[CH:20]=[CH:19][C:13]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)[C:7]([NH2:9])=[NH:8].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:36][S:37]([O:40][C:41]1[CH:50]=[CH:49][C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:51](=[NH:53])[NH2:52])[CH:47]=2)[CH:42]=1)(=[O:39])=[O:38]>N1C=CC=CC=1>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].[NH:6]([C:10]1[CH:20]=[CH:19][C:13]([CH:14]=[CH:15][C:16]([O:18][C:41]2[CH:50]=[CH:49][C:48]3[C:43](=[CH:44][CH:45]=[C:46]([C:51](=[NH:52])[NH2:53])[CH:47]=3)[CH:42]=2)=[O:17])=[CH:12][CH:11]=1)[C:7]([NH2:9])=[NH:8]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonateHCID 178505352HCID 178505352, compound

Product 1

HCID 178505336HCID 178505336, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.0 g of 4-guanidinocinnamic acid methanesulfonate in 30 ml of anhydrous pyridine, was added 2.4 g of DCC. To the mixture, while being cooled in ice and stirred, was added 2.8 g of 6-amidino-2-naphthol methanesulfonate. After having been stirred for 24 hours, the reaction mixture was filtered to remove insolubles and the filtrate was mixed with ethyl ether to separate an only substance which was left standing at room temperature to crystallize. Upon recrystallization from a methanol-ethyl ether mixture, there was obtained 2.4 g of 6-amidino-2-naphthyl 4-guanidinocinnamate dimethanesulfonate.

Workup

  1. temperatureTo the mixture, while being cooled in ice
  2. stirringAfter having been stirred for 24 hours
  3. filtrationthe reaction mixture was filtered
  4. customto remove insolubles
  5. additionthe filtrate was mixed with ethyl ether
  6. customto separate an only substance which
  7. waitwas left
  8. customstanding at room temperature
  9. customto crystallize
  10. customUpon recrystallization from a methanol-ethyl ether mixture

Sources & evidence

ORD record
ord-6cd22e34fae844c6bd49e3ee0b8419c3
Source dataset
uspto-grants-1984_06
Patent number
US04454338

Reaction notes

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