Carbon Dioxide → HCID 23707837, compound

HRID 902877Notes

Reaction equation

HRID 902877 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>[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.[Li+:17]

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 ethyleneacetal (J. Chem. Soc. Perkin Trans. 1, 1992, p. 973) (2.26 g) was dissolved in tetrahydrofuran (15 ml), and n-butyllithium (1.5N hexane solution, 6.8 ml) was added under cooling with dry ice-acetone to stir the mixture for 20 minutes. At the same temperature, carbon dioxide was then introduced. The reaction mixture was gradually heated to room temperature over 1.5 hours and then concentrated. Hexane was added to the reaction mixture to powder the product. The product was collected by filtration and suspended in ethyl acetate, and formed powder was collected again by filtration to obtain the title compound (1.65 g).

Workup

  1. concentrationconcentrated
  2. additionHexane was added to the reaction mixture to powder the product
  3. filtrationThe product was collected by filtration
  4. customformed powder
  5. filtrationwas collected again by filtration

Sources & evidence

ORD record
ord-10c413376e2249b98431dcef6b15504f
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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