Methanol → HCID 13178451, compound

HRID 1981424Notes

Reaction equation

HRID 1981424 reaction equation
CO.CS(O)(=O)=O.CS(O)(=O)=O.[C:13]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[NH:30])[NH2:29])=[CH:24][C:23]=1[C:31]([OH:33])=[O:32])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)C>[C:13]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[NH:29])[NH2:30])=[CH:24][C:23]=1[C:31]([OH:33])=[O:32])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 86740071HCID 86740071, compound

Product 1

HCID 13178451HCID 13178451, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 3.0 g of 5-amidinosalicylic acid methanesulfonate in 40 ml of dried pyridine, while being cooled in ice and stirred, was added slowly 1.5 g of benzoyl chloride. The mixture was stirred for 3 hours at room temperature. The crystals gradually dissolved, forming a clear pale yellow solution, and an oily substance separated out. After addition of ethyl ether to the reaction mixture and removal of the supernatant, the oily substance was washed several times with ethyl ether and dissolved in water. Upon addition of a saturated aqueous sodium hydrogencarbonate solution, pale yellow crystals precipitated. After cooling in ice, the crystals were collected by filtration, washed with a small volume of water, and dried to obtain 1.0 g of the crystals. The crystals were suspended in a small volume of methanol and allowed to dissolve by the addition of 0.4 g of methanesulfonic acid. Ethyl ether was added to the solution with stirring to obtain 0.8 g of a colorless powder of 4-amidino-2-carboxyphenyl benzoate methanesulfonate.

Sources & evidence

ORD record
ord-087f28d2533e4865a31d4c48c0e575ed
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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