Carbon Dioxide → Lithium 4-(morpholinomethyl)thiazole-2-carboxylate

HRID 546431Notes

Reaction equation

HRID 546431 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[N:9]=[CH:10][S:11][CH:12]=2)[CH2:3][CH2:2]1.[C:13](=[O:15])=[O:14].C([Li:20])CCC>C(OCC)C>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[N:9]=[C:10]([C:13]([O-:15])=[O:14])[S:11][CH:12]=2)[CH2:3][CH2:2]1.[Li+:20]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 178425104-(Morpholinomethyl)thiazoleHCID 178418339Butyllithium

Product 1

HCID 23712808Lithium 4-(morpholinomethyl)thiazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

4-(Morpholinomethyl)thiazole (640 mg) was dissolved in diethyl ether (5 ml) in an argon atmosphere, and n-butyllithium (1.54N hexane solution, 2.50 ml) was added dropwise at −78° C. The reaction mixture was stirred for 10 minutes under ice cooling, and cooled again to −78° C. After blowing carbon dioxide into the reaction mixture for 20 minutes, it was heated to room temperature. The reaction mixture was concentrated under reduced pressure to obtain the title compound (873 mg) as crude yellow powder.

Workup

  1. additionwas added dropwise at −78° C
  2. customfor 20 minutes
  3. temperatureit was heated to room temperature
  4. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-64b8271cb2164c2a9604aa0661facf5e
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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