Phosphorus oxychloride → 8-Acetamidoquinoline-5-sulfonyl chloride

HRID 2412827Notes

Reaction equation

HRID 2412827 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([NH:9][C:10]1[C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]([S:20]([O-:23])(=O)=[O:21])=[CH:12][CH:11]=1)(=[O:8])[CH3:7].[NH+]1C=CC=CC=1>CN1CCCC1=O>[C:6]([NH:9][C:10]1[C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]([S:20]([Cl:3])(=[O:23])=[O:21])=[CH:12][CH:11]=1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20431103HCID 20431103, compound

Product 1

HCID 204310978-Acetamidoquinoline-5-sulfonyl chlorideYield 94%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 1 liter 3-neck round bottomed flask, fitted with a mechanical stirrer and a calcium chloride drying tube, phosphorus oxychloride (360 ml) was chilled to less than 10° C. N-methylpyrrolidone (20 ml) was added (slight exotherm). When the temperature returned to <5° C., finely ground pyridinium 8-acetamido-5-quinolinesulfonate (36.0 g, 0.104 mole) was added. The reaction mixture was thoroughly packed in ice and stirred for 20 hrs. The resulting brown slurry was slowly added to ca. 2500 ml ice/water (cooled by an external ice-salt bath) with vigorous stirring. After stirring for one hour the product was collected by filtration and yielded 27.9 g (94 percent) of a tan powder, m.p. 203°-204° C. (decomp.).

Workup

  1. customIn a 1 liter 3-neck round bottomed flask, fitted with a mechanical stirrer and a calcium chloride drying tube
  2. customreturned to <5° C.
  3. stirringAfter stirring for one hour the product
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e1f4ecafdc904425920078be78d375c7
Source dataset
uspto-grants-1985_01
Patent number
US04495100

Reaction notes

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