3-Methylbenzoic acid → 6-Amidino-2-naphthyl 3-methylbenzoate methanesulfonate

HRID 371423Notes

Reaction equation

HRID 371423 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:26][S:27]([O:30][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:29])=[O:28]>N1C=CC=CC=1>[CH3:26][S:27]([OH:30])(=[O:29])=[O:28].[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][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:6]

Participants

5

Reactant 3

HCID 74183-Methylbenzoic acidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 131768556-Amidino-2-naphthyl 3-methylbenzoate methanesulfonateYield 32.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.3 g of m-methylbenzoic acid in 30 ml of anhydrous pyridine, was added 4.4 g of DCC. To the stirred mixture, while being cooled in ice, was added 5 g of 6-amidino-2-naphthol methanesulfonate. After stirring for 24 hours, the insolubles were removed by filtration and ethylether was added to the filtrate. On separation of the resulting oily substance by decantation, it crystallized. The crystals were recrystallized from a methanol-ether mixture to obtain 2.2 g of 6-amidino-2-naphthyl 3-methylbenzoate methanesulfonate.

Workup

  1. temperatureTo the stirred mixture, while being cooled in ice
  2. customthe insolubles were removed by filtration and ethylether
  3. additionwas added to the filtrate
  4. customOn separation of the resulting oily substance by decantation, it
  5. customcrystallized
  6. customThe crystals were recrystallized from a methanol-ether mixture

Sources & evidence

ORD record
ord-ec500a5407db4840a42e7d19edbc3bfb
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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