Dicyclohexylcarbodiimide → HCID 86742467, compound

HRID 620221Notes

Reaction equation

HRID 620221 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[CH2:10][CH2:9][N:8]=[CH:7]1.[CH3:21][S:22]([O:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36](=[NH:38])[NH2:37])[CH:32]=2)[CH:27]=1)(=[O:24])=[O:23].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:21][S:22]([OH:25])(=[O:24])=[O:23].[N:6]1([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:36](=[NH:37])[NH2:38])[CH:32]=4)[CH:27]=3)=[O:17])=[CH:19][CH:20]=2)[CH2:10][CH2:9][N:8]=[CH:7]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonateHCID 86742469HCID 86742469, compound

Product 1

HCID 86742467HCID 86742467, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 1.03 g of 4-(2-imidazolinyl)amino-benzoic acid methanesulfonate, 0.96 g of 6-amidino-2-naphthol methanesulfonate, 42 mg of DMAP and 1.06 g of DCC was added 5 ml of anhydrous pyridine. The resulting mixture was stirred overnight at room temperature. To the mixture was added 50 ml of aceone and the precipitate which was formed was collected by filtration. To the precipitate was added 40 ml of DMF. After stirring the precipitate which was formed was collected by filtration and 20 ml of water was added to the precipitate. The insolubles were removed by filtration. The filtrate was distilled under reduced pressure. To the residue was added 200 ml of acetone. The precipitate which was formed was collected by filtration to obtain 0.8 g of 6-amidino-2-naphthyl 4-(2-imidazolinyl)amino-benzoate dimethanesulfonate.

Workup

  1. additionTo the mixture was added 50 ml of aceone
  2. customthe precipitate which was formed
  3. filtrationwas collected by filtration
  4. additionTo the precipitate was added 40 ml of DMF
  5. stirringAfter stirring the precipitate which
  6. customwas formed
  7. filtrationwas collected by filtration and 20 ml of water
  8. additionwas added to the precipitate
  9. customThe insolubles were removed by filtration
  10. distillationThe filtrate was distilled under reduced pressure
  11. additionTo the residue was added 200 ml of acetone
  12. customThe precipitate which was formed
  13. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f4b6c221493b44efb08e9babecdfa182
Source dataset
uspto-grants-1989_04
Patent number
US04820730

Reaction notes

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