Carbon Dioxide → HCID 23707837, compound

HRID 2104404Notes

Reaction equation

HRID 2104404 reaction equation
[CH2:1]1[O:12][CH:4]([C:5]2[S:9][C:8](Cl)=[N:7][C:6]=2[Cl:11])[O:3][CH2:2]1.C([Li:17])CCC.[C:18](=[O:20])=[O:19].CC(C)=O.C(=O)=O>O1CCCC1>[Li+:17].[Cl:11][C:6]1[N:7]=[C:8]([C:18]([O-:20])=[O:19])[S:9][C:5]=1[CH:4]1[O:12][CH2:1][CH2:2][O:3]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 15665807HCID 15665807, compoundHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 23707837HCID 23707837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dichlorothiazole-5-carbaldehyde ethylene acetal (J. Chem. Soc. Perkin Trans. 1, p. 973 (1992)) (2.26 g) was dissolved in tetrahydrofuran (15 mL), and n-butyllithium (as 1.5N hexane solution, 6.8 mL) was added thereto while being cooled with dry ice-acetone. After the reaction mixture was stirred for 20 minutes, carbon dioxide gas was introduced into the mixture at the same temperature. The reaction mixture was gradually heated to room temperature over 1.5 hours, and the mixture was concentrated under reduced pressure. Hexane was added to the residue, and the resultant powder was collected by filtration. The powder was suspended in ethyl acetate, and the powder was collected by filtration again, to thereby give the title compound (1.65 g).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionHexane was added to the residue
  3. filtrationthe resultant powder was collected by filtration
  4. filtrationthe powder was collected by filtration again

Sources & evidence

ORD record
ord-8bc3f401a6c74307807f8e486b85dc75
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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