Carbon Dioxide → Lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

HRID 352861Notes

Reaction equation

HRID 352861 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][C:5]2[S:8][CH:9]=[N:10][C:4]=2[CH2:3]1.C([Li:15])CCC.[C:16](=[O:18])=[O:17]>O1CCCC1.CCCCCC>[CH3:1][CH:2]1[NH:7][CH2:6][C:5]2[S:8][C:9]([C:16]([O-:18])=[O:17])=[N:10][C:4]=2[CH2:3]1.[Li+:15]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 227111356-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridineHCID 178418339Butyllithium

Product 1

HCID 23674323Lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

In anhydrous tetrahydrofuran (200 ml), 6-methyl -4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (6.43 g) was dissolved, followed by the dropwise addition of a solution (1.47M, 34.00 ml) of n-butyl lithium in n-hexane at an external temperature of −78° C. The resulting mixture was stirred for 40 minutes without changing the temperature. Then a carbon dioxide gas was blown into the reaction mixture for 1 hour. After warming up to room temperature, the reaction mixture was concentrated under reduced pressure, whereby the title compound (9.42 g, quant.) was obtained as a pale brown foamy solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure, whereby the title compound (9.42 g, quant.)
  2. customwas obtained as a pale brown foamy solid

Sources & evidence

ORD record
ord-18381ee1c53a4f4a85ec76f1484d95bf
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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