Potassium Bicarbonate → HCID 10029739, compound

HRID 1533861Notes

Reaction equation

HRID 1533861 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]([OH:28])=[O:27])[C:5]2=[O:29].C(=O)(O)[O-].[K+].Br[CH2:36][C:37]1[O:38][C:39](=[O:43])[O:40][C:41]=1[CH3:42]>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]([CH2:36][C:37]3[O:38][C:39](=[O:43])[O:40][C:41]=3[CH3:42])[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]([OH:28])=[O:27])[C:5]2=[O:29]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 10476724HCID 10476724, compoundHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

Product 1

HCID 10029739HCID 10029739, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Fluoro-4-oxo-1-phenyl-7-(1-piperazinyl)-4H-[1,3]-thiazeto-[3,2-a]quinoline-3-carboxylic acid (3.0 g) and 0.88 g of potassium bicarbonate were suspended in 50 ml of N,N-dimethylformamide, 1.69 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 into ice water, the crystals separated out therefrom was collected by filtration, washed with water, dried in vacuo, and the resulting crude crystals were recrystallized from chloroform-ethanol to give 1.3 g of desired product, m.p.201°-202° C. (decompn.).

Workup

  1. customAfter the reaction
  2. customthe crystals separated out
  3. filtrationtherefrom was collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customthe resulting crude crystals were recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-504023bf18d94e03aec16deb863af266
Source dataset
uspto-grants-1992_02
Patent number
US05086049

Reaction notes

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