Methanesulfonic Acid → HCID 178512130, compound

HRID 1154583Notes

Reaction equation

HRID 1154583 reaction equation
Cl.[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:35]1[CH:40]=[CH:39][C:38]([CH:41]=[CH:42][C:43](=[NH:45])[NH2:44])=[CH:37][CH:36]=1)(=O)=O.CS(O)(=O)=O>N1C=CC=CC=1.C(OCC)C>[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][C:35]2[CH:40]=[CH:39][C:38]([CH:41]=[CH:42][C:43](=[NH:44])[NH2:45])=[CH:37][CH:36]=2)=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4]

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10868DicyclohexylcarbodiimideHCID 54417104HCID 54417104, compoundHCID 178479383HCID 178479383, compound

Product 1

HCID 178512130HCID 178512130, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 106 g of 4-guanidinobenzoic acid hydrochloride in 1.3 liters of pyridine, while being cooled in ice and stirred, was added 122 g of DCC. After 30 minutes of stirring, to the mixture was added slowly 127 g of 4-(β-amidinoethenyl)phenol methanesulfonate. The resulting clear solution was stirred overnight and the precipitated solid substance was collected by filtration. The solid substance was suspended in 2 liters of water, thoroughly stirred, and filtered. To the filtrate was added at room temperature about 2 liters of saturated aqueous sodium bicarbonate solution. The mixture was stirred and the precipitated crystals were collected by filtration, washed with water, and then with acetone. After air-drying for a short time, the orange-yellow crystals were suspended in 200 ml of methanol and admixed with about 100 g (2 equivalents) of methanesulfonic acid while stirring at room temperature. Ethyl ether was added to the reaction mixture to precipitate crystals which were collected by filtration. The crystals were suspended in methanol and converted again to the carbonate. The carbonate was suspended in 300 ml of ethanol at room temperature and admixed with methanesulfonic acid to turn the suspension into a clear solution. The solution was stirred for a while to precipitate crystals which were collected by filtration at room temperature and thoroughly washed with cold ethanol. The yield was 45 g (18%).

Workup

  1. stirringAfter 30 minutes of stirring, to the mixture
  2. stirringThe resulting clear solution was stirred overnight
  3. filtrationthe precipitated solid substance was collected by filtration
  4. stirringthoroughly stirred
  5. filtrationfiltered
  6. additionTo the filtrate was added at room temperature about 2 liters of saturated aqueous sodium bicarbonate solution
  7. stirringThe mixture was stirred
  8. filtrationthe precipitated crystals were collected by filtration
  9. washwashed with water
  10. customAfter air-drying for a short time
  11. stirringwhile stirring at room temperature
  12. customto precipitate crystals which
  13. filtrationwere collected by filtration
  14. customwas suspended in 300 ml of ethanol at room temperature
  15. stirringThe solution was stirred for a while
  16. customto precipitate crystals which
  17. filtrationwere collected by filtration at room temperature
  18. washthoroughly washed with cold ethanol

Sources & evidence

ORD record
ord-80107e6f685b469597e548cdf6361bf5
Source dataset
uspto-grants-1984_12
Patent number
US04490388

Reaction notes

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