Diethyl Ether → HCID 13178454, compound

HRID 1981431Notes

Reaction equation

HRID 1981431 reaction equation
C(=O)([O-])[O-].CS(O)(=O)=O.C(OCC)C.CS(O)(=O)=O.[C:20]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[NH:37])[NH2:36])=[CH:31][C:30]=1[N+:38]([O-:40])=[O:39])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[C:20]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[NH:36])[NH2:37])=[CH:31][C:30]=1[N+:38]([O-:40])=[O:39])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 19660Carbonate IonHCID 86740075HCID 86740075, compound

Product 1

HCID 13178454HCID 13178454, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into 40 ml of dried pyridine, was dissolved 4.2 g of 4-amidino-2-nitrophenol methanesulfonate. To the solution, while being cooled in ice and stirred, was added portionwise 2.1 g of benzoyl chloride. The solution was stirred overnight at room temperature and removed of the insolubles by filtration. Ethyl ether was added to the filtrate to allow an oily substance to separate out. After removal of the supernatant, the oily substance was washed a few times with ethyl ether, and dissolved in water. To the aqueous solution, while being stirred, was added a saturated aqueous sodium hydrogencarbonate solution to precipitate the carbonate of the captioned compound. The carbonate precipitate was collected by filtration, washed with water, then with acetone, and dried to obtain 4.0 g of pale yellow crystals. To the carbonate crystals suspended in 10 ml of methanol, was added 1.4 g of methanesulfonic acid. The mixture turned, with effervescence, into a homogeneous solution. Upon addition of ethyl ether there were obtained 4.1 g of colorless granular crystals of 4-amidino-2-nitrophenyl benzoate methanesulfonate.

Sources & evidence

ORD record
ord-ec898e2e65694e64b99ba92db7f16d39
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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