2-Methylbenzoic acid → HCID 13176852, compound

HRID 371422Notes

Reaction equation

HRID 371422 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:43])[NH2:42])[CH:37]=2)[CH:32]=1)(=O)=O>N1C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:42])[NH2:43])[CH:37]=2)[CH:32]=1)=[O:5]

Participants

5

Reactant 3

HCID 83732-Methylbenzoic acidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13176852HCID 13176852, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 50 ml of anhydrous pyridine, was added 2.4 g of 2-methylbenzoic acid followed by 4.4 g of DCC under cooling in ice. After stirring for 30 minute and adding 5.0 g of 6-amidino-2-naphthol methanesulfonate, the mixture was stirred overnight at room temperature. The precipitate was collected by filtration and washed with a small volume of pyridine, then successively with ethylether and acetone. The precipitate was dissolved in DMF and the insolubles were removed by filtration. Ethylether was added to the filtrate and the precipitated crystals were recrystallized from ethanol to obtain 1.4 g of flaky colorless crystals of 6-amidino-2-naphthyl 2-methyl benzoate methanesulfonate.

Workup

  1. temperatureunder cooling in ice
  2. stirringthe mixture was stirred overnight at room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with a small volume of pyridine
  5. dissolutionThe precipitate was dissolved in DMF
  6. customthe insolubles were removed by filtration
  7. additionEthylether was added to the filtrate
  8. customthe precipitated crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-01170e52de4f4901991e79f9b6d0ed7a
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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