Dicyclohexylcarbodiimide → HCID 178512531, compound

HRID 371432Notes

Reaction equation

HRID 371432 reaction equation
Cl.[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4].C1CCC(N=C=NC2CCCCC2)CC1.CS([O:34][C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:45](=[NH:47])[NH2:46])[CH:41]=2)[CH:36]=1)(=O)=[O:32]>N1C=CC=CC=1>[C:10](=[O:11])([OH:32])[OH:12].[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:34][C:35]2[CH:44]=[CH:43][C:42]3[C:37](=[CH:38][CH:39]=[C:40]([C:45](=[NH:47])[NH2:46])[CH:41]=3)[CH:36]=2)=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonateHCID 178479383HCID 178479383, compound

Product 1

HCID 178512531HCID 178512531, compoundYield 183.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To 100 ml of pyridine, were added 8.6 g of 4-guanidinobenzoic acid hydrochloride and 9.0 g of DCC. The mixture was stirred for one hour under cooling in ice (reaction mixture A). To 100 ml of pyridine, was added 113 g of 6-amidino-2-naphthol methanesulfonate. To the mixture, while being cooled in ice and stirred, was added the reaction mixture A portionwise over a period of one hour. After completion of the addition, the resulting mixture was stirred for another hour under cooling in ice, then overnight at room temperature. The precipitated crystals were collected by filtration and washed with pyridine and acetone. The crystals were then dissolved in about 200 ml of water and the insoluble DCU was removed by filtration. A saturated aqueous sodium hydrogencarbonate solution was added to the filtrate to precipitate pale yellow crystals. The crystals were washed with water and acetone to obtain 15 g (79.8% yield) of 6-amidino-2-naphthyl 4-guanidinobenzoate carbonate. From this carbonate other acid addition salts may be obtained by the procedure described in method A.

Workup

  1. temperatureunder cooling in ice (
  2. customreaction mixture A)
  3. temperatureTo the mixture, while being cooled in ice
  4. stirringstirred
  5. additionwas added the reaction mixture A portionwise over a period of one hour
  6. additionAfter completion of the addition
  7. stirringthe resulting mixture was stirred for another hour
  8. temperatureunder cooling in ice
  9. customovernight
  10. customat room temperature
  11. filtrationThe precipitated crystals were collected by filtration
  12. washwashed with pyridine and acetone
  13. dissolutionThe crystals were then dissolved in about 200 ml of water
  14. customthe insoluble DCU was removed by filtration
  15. additionA saturated aqueous sodium hydrogencarbonate solution was added to the filtrate
  16. customto precipitate pale yellow crystals
  17. washThe crystals were washed with water and acetone

Sources & evidence

ORD record
ord-c21bbb847c2d4c55bfbde9baef28a215
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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