Pyridine → HCID 86740074, compound

HRID 1981429Notes

Reaction equation

HRID 1981429 reaction equation
N1C=CC=CC=1.[CH3:7][S:8]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[NH:20])[NH2:19])=[CH:14][C:13]=1[Cl:21])(=[O:10])=[O:9].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)C>[CH3:7][S:8]([OH:11])(=[O:10])=[O:9].[C:22]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[NH:20])[NH2:19])=[CH:14][C:13]=1[Cl:21])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 53931603HCID 53931603, compound

Product 1

HCID 86740074HCID 86740074, compoundYield 124.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 30 ml of anhydrous pyridine, was added 2.7 g of 4-amidino-2-chlorophenol methanesulfonate. To the mixture, while being cooled in ice, was added 1.4 g of benzoyl chloride. The mixture was stirred for 30 minutes, while being cooled in ice, then for 5 hours at room temperature. The reaction mixture was mixed with 100 ml of ethyl ether to allow an oily substance to separate out. The oily substance was dissolved in 20 ml of methanol and poured into a saturated aqueous sodium hydrogencarbonate solution. The precpitated crystals were collected by filtration and washed with water, then with acetone. The washed crystals were added to 20 ml of methanol and admixed with 2.5 g of methanesulfonic acid. The insolubles were removed by filtration and 100 ml of ethyl ether was added to the filtrate. The precipitated colorless crystals were collected by filtration to obtain 2.5 g of 4-amidino-2-chlorophenyl benzoate methanesulfonate.

Workup

  1. temperatureTo the mixture, while being cooled in ice
  2. temperaturewhile being cooled in ice
  3. waitfor 5 hours at room temperature
  4. customto separate out
  5. dissolutionThe oily substance was dissolved in 20 ml of methanol
  6. additionpoured into a saturated aqueous sodium hydrogencarbonate solution
  7. filtrationThe precpitated crystals were collected by filtration
  8. washwashed with water
  9. additionThe washed crystals were added to 20 ml of methanol
  10. customThe insolubles were removed by filtration and 100 ml of ethyl ether
  11. additionwas added to the filtrate
  12. filtrationThe precipitated colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-e1ce39fa97ef46debacd17e01a17ad0a
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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