Potassium Carbonate → HCID 13259513, compound

HRID 2295723Notes

Reaction equation

[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:20])[C:7]([C:17]([OH:19])=[O:18])=[C:8]4[S:16][CH2:15][CH2:14][N:9]43)=[CH:4][C:3]=2[O:2]1.C(=O)([O-])[O-].[K+].[K+].[C:27]([O:33][CH2:34]Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:20])[C:7]([C:17]([O:19][CH2:34][O:33][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:18])=[C:8]4[S:16][CH2:15][CH2:14][N:9]43)=[CH:4][C:3]=2[O:2]1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 87885Chloromethyl pivalate

HCID 13116422HCID 13116422, compound

Product 1

HCID 13259513HCID 13259513, compoundYield 71.9%

Conditions

Temperature: 100 °C

Procedure

7,8-Methylenedioxy-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylic acid (200 mg, 0.687 mmol) was dissolved in 5 ml of dimethyl formaide, then 152 mg of anhydrous potassium carbonate (1.1 mmol) and 328 mg (2.18 mmol) of pivaloyloxymethyl chloride were added thereto, the mixture was heated with stirring at 100° C. for six hours, the content was concentrated under reduced pressure, water was added to the residue, then insoluble matter was collected by filtration, washed with water, air dried and recrystallized from a mixture of chloroform and ether to give 200 mg of the title compound (71.9 percent yield). Melting point 229.0° to 229.5° C. Elementary analysis calculated as C19H19NO7S.1/4 H2O: C 55.67, H 4.79, N 3.42; Found: C 55.65, H 4.59, N 3.49.

Workup

temperaturethe mixture was heated
concentrationthe content was concentrated under reduced pressure, water
additionwas added to the residue
filtrationinsoluble matter was collected by filtration
washwashed with water, air
customdried
customrecrystallized from a mixture of chloroform and ether

Sources & evidence

ORD record: ord-33bf60c8441b485c8959474ff316511c
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04426381

Reaction notes

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