Potassium Bicarbonate → HCID 14721208, compound

HRID 1533862Notes

Reaction equation

HRID 1533862 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[N:8]1[CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:19][C:7]1=[C:6]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5]2=[O:31].C(=O)(O)[O-].[K+].Br[CH2:38][C:39]1[O:40][C:41](=[O:45])[O:42][C:43]=1[CH3:44]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:38][C:39]3[O:40][C:41](=[O:45])[O:42][C:43]=3[CH3:44])[CH2:14][CH2:13]1)[N:8]1[CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:19][C:7]1=[C:6]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5]2=[O:31]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 10048830HCID 10048830, compoundHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

Product 1

HCID 14721208HCID 14721208, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 6-fluoro-4-oxo-1-phenyl-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate (3.0 g) and 0.82 g of potasium bicarbonate were suspended in 50 ml of N,N-dimethylformamide, 1.58 g of 4-bromomethyl-5-methyl-1,3-dioxolen-2-one was dropped thereinto with ice cooling, and the mixture was stirred for 3 hours. After the reaction, the mixture was poured over into ice water and the crystals separated out therefrom were collected by filtration. They were then dissolved in chloroform, the solution was washed with water, and evaporated/dried in vacuo. The resulting oily residue was purified by a column chromatography (silica gel/methanolchloroform [1:50]) to give 2.47 g of desired product, mp, 223°-226° C. (decompn.).

Workup

  1. customAfter the reaction
  2. customthe crystals separated out
  3. filtrationtherefrom were collected by filtration
  4. dissolutionThey were then dissolved in chloroform
  5. washthe solution was washed with water
  6. customevaporated/dried in vacuo
  7. customThe resulting oily residue was purified by a column chromatography (silica gel/methanolchloroform [1:50])

Sources & evidence

ORD record
ord-1225473510194d808b8d220521cbbf63
Source dataset
uspto-grants-1992_02
Patent number
US05086049

Reaction notes

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