HCID 54072559, compound → HCID 13116417, compound

HRID 2295720Notes

Reaction equation

HRID 2295720 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]([CH3:14])[CH2:12][S:11][C:10]2=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16](OCC)=[O:17])[CH:5]=[CH:6][C:7]=1[F:8]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:16](=[O:17])[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:10]3[S:11][CH2:12][CH:13]([CH3:14])[N:9]32)=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 1

HCID 54072559HCID 54072559, compound

Product 1

HCID 13116417HCID 13116417, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

Diethyl 3-(3-bromo-4-fluorophenyl)-4-methyl-1,3-thiazolidin-2-ylidenemalonate (4.2 grams) was dissolved in 40 grams of polyphosphoric acid and the solution was heated with stirring at 90° C. for three hours. After the reaction, the content was poured over into ice water and extracted with chloroform to give 3.5 grams of sirupy substance. This was subjected to a column chromatography on 350 grams of silica gel using chloroform as a developer and, from the initial distillate, 620 mg of ethyl 8-bromo-7-fluoro-1-methyl-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a) quinoline 4-carboxylate was obtained, Melting point was 211° C.

Workup

  1. temperaturethe solution was heated
  2. customAfter the reaction
  3. extractionextracted with chloroform
  4. customto give 3.5 grams of sirupy substance

Sources & evidence

ORD record
ord-5e08039fd2824dfa80dc03adc88f17ef
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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