Methanesulfonic Acid → HCID 54492772, compound

HRID 1981439Notes

Reaction equation

HRID 1981439 reaction equation
CS(O)(=O)=O.C(=O)([O-])[O-].CS(O)(=O)=O.[C:15]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[NH:34])[NH2:33])=[CH:28][C:27]=1[O:35][CH3:36])(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[C:15]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[NH:33])[NH2:34])=[CH:28][C:27]=1[O:35][CH3:36])(=[O:24])[CH:16]=[CH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 19660Carbonate Ion2×HCID 86740078HCID 86740078, compound

Product 1

HCID 54492772HCID 54492772, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6.2 g of 4-amidino-2-methoxyphenol methanesulfonate in 30 ml of dried pyridine, while being cooled in ice and stirred, was added 3.9 g of cinnamoyl chloride. Immediately after the addition a colorless solid substance precipitated from the reaction mixture. After 3 hours of stirring at room temperature, ethyl ether was added to the mixture and the precipitate was collected by filtration. The precipitate was dissolved in methanol and mixed with a saturated aqueous sodium bicarbonate solution to precipitate a white gelatinous substance. The gelatinous substance was collected by filtration, washed with water, then with acetone and dried to obtain 6.3 g of the carbonate of the captioned compound. Upon addition of 2.3 g of methanesulfonic acid to the carbonate suspended in 60 ml of methanol, a change in crystal form of the carbonate took place accompanied by effervescence. The suspension was heated to dissolve the crystals and then cooled to obtain 6.3 g of colorless needle crystals of 4-amidino-2-methoxyphenyl cinnamate methanesulfonate.

Workup

  1. temperatureThe suspension was heated
  2. dissolutionto dissolve the crystals
  3. temperaturecooled

Sources & evidence

ORD record
ord-7b291b21d91844aba55495f7a8b9c992
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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