Dicyclohexylcarbodiimide → 6-Amidino-2-naphthyl 3-dimethylaminobenzoate carbonate

HRID 371428Notes

Reaction equation

HRID 371428 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].C1CCC(N=C=NC2CCCCC2)CC1.CS([O:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:43](=[NH:45])[NH2:44])[CH:39]=2)[CH:34]=1)(=O)=[O:30]>N1C=CC=CC=1>[C:6](=[O:7])([OH:30])[OH:8].[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:43](=[NH:45])[NH2:44])[CH:39]=2)[CH:34]=1)=[O:7]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 668373-(Dimethylamino)benzoic acidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 131768906-Amidino-2-naphthyl 3-dimethylaminobenzoate carbonateYield 109.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 70 ml of dried pyridine, were added 2.9 g of 3-dimethylaminobenzoic acid and 4.4 g of DCC. The mixture was stirred for 30 minutes while cooling in ice. After addition of 5.0 g of 6-amidino-2-naphthol methanesulfonate, the mixture was further stirred for one hour under cooling in ice and then overnight at room temperature. The reaction mixture was filtered and the filtrate was mixed with ethyl ether. The precipitate which was formed was collected by filtration, dissolved in a small quantity of methanol, and added to a saturated aqueous sodium hydrogencarbonate solution while being stirred. The precipitated crystals were collected by filtration to obtain 3.8 g of 6-amidino-2-naphthyl 3-dimethylaminobenzoate carbonate having a melting point of above 120° C. (decomp.). The crystals were suspended in ethanol, mixed with 1.4 g of acetic acid and stirred to form a clear solution from which crystals were precipitated after some time. The crystals were collected by filtration and recrystallized from ethanol to obtain 2.5 g of a white powder of 6-amidino-2-naphthyl 3-dimethylaminobenzoate acetate.

Workup

  1. temperaturewhile cooling in ice
  2. stirringthe mixture was further stirred for one hour
  3. temperatureunder cooling in ice
  4. customovernight
  5. customat room temperature
  6. filtrationThe reaction mixture was filtered
  7. additionthe filtrate was mixed with ethyl ether
  8. customThe precipitate which was formed
  9. filtrationwas collected by filtration
  10. dissolutiondissolved in a small quantity of methanol
  11. additionadded to a saturated aqueous sodium hydrogencarbonate solution
  12. stirringwhile being stirred
  13. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-e0190d08a91e45f5819f6186c575c3c1
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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