Diethyl Ether → HCID 13146244, compound

HRID 2413216Notes

Reaction equation

HRID 2413216 reaction equation
CS(O)(=O)=O.C(OCC)C.CS(O)(=O)=O.[CH:16]1([C:19]([O:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:32](=[NH:34])[NH2:33])[CH:28]=3)[CH:23]=2)=[O:20])[CH2:18][CH2:17]1>CO>[CH:16]1([C:19]([O:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:32](=[NH:33])[NH2:34])[CH:28]=3)[CH:23]=2)=[O:20])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 13146245HCID 13146245, compound

Product 1

HCID 13146244HCID 13146244, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.0 g of 6-amidino-2-naphthol methanesulfonate in 50 ml of anhydrous pyridine, while being cooled in ice, was added dropwise with stirring 1.9 g of cyclopropanecarbonyl chloride. The mixture was stirred overnight at room temperature, and the insolubles were separated and washed with a small volume of pyridine. The filtrate and the washings were poured into stirred ethyl ether. The crystals were collected by filtration, washed with ethyl ether, dissolved in water, and poured into stirred saturated aqueous sodium bicarbonate solution. The precipitated crystals were collected by filtration, washed with water, then with acetone, and dried to obtain 3.4 g of the carbonate of the captioned compound. To a suspension of the salt in 20 ml of methanol, while being cooled in ice, was added 1.2 equivalents of methanesulfonic acid followed by ethyl ether to obtain 3.0 g of white granular crystals of 6-amidino-2-naphthyl cyclopropanecarboxylate methanesulfonate.

Workup

  1. temperaturewhile being cooled in ice

Sources & evidence

ORD record
ord-9f6593af95cc4690a21a850138ca7b40
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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