Carbon Dioxide → HCID 13118865, compound

HRID 1073210Notes

Reaction equation

HRID 1073210 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([CH:9]=1)[C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[S:5]2.C([Li])CCC.[C:19](=[O:21])=[O:20].[OH-].[Na+]>O1CCCC1.CCCCCC>[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9]=1[C:19]([OH:21])=[O:20])[C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[S:5]2

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 336507NSC351165HCID 178418339Butyllithium

Product 1

HCID 13118865HCID 13118865, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-Methylimidazo[2,1-b]benzothiazole, 18.8 g, was suspended in 100 ml of dry tetrahydrofuran. Under cooling (at -78° C.), 100 ml of a solution of n-butyl lithium in n-hexane was dropwise added to the suspension over 15 minutes. After completion of the dropwise addition, the temperature was gradually raised and stirring was performed at 0° C. for 30 minutes. The mixture was again cooled to -78° C. After adding an excess of dry ice, the temperature was gradually raised and stirring was performed at 0° C. for 30 minutes. Under ice cooling, 200 ml of 2N sodium hydroxide solution was added to the reaction solution. After washing with ether, the aqueous phase was neutralized with acetic acid and the precipitated crystals were taken out by filtration. The crystals were stirred in 300 ml of chloroform for 30 minutes and 6.0 g of 2-methylimidazo[2,1-b]benzothiazole-3-carboxylic acid was obtained as the insoluble matter in chloroform.

Workup

  1. additionwas dropwise added to the suspension over 15 minutes
  2. additionAfter completion of the dropwise addition
  3. temperaturethe temperature was gradually raised
  4. temperaturethe temperature was gradually raised
  5. stirringstirring
  6. waitwas performed at 0° C. for 30 minutes
  7. washAfter washing with ether
  8. filtrationthe precipitated crystals were taken out by filtration
  9. stirringThe crystals were stirred in 300 ml of chloroform for 30 minutes

Sources & evidence

ORD record
ord-46cbf835c326441da8be076fc82f9acf
Source dataset
uspto-grants-1990_11
Patent number
US04968708

Reaction notes

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