Oxalyl chloride → HCID 44236097, compound

HRID 2404005Notes

Reaction equation

HRID 2404005 reaction equation
C(Cl)(=O)C(Cl)=O.[O:7]=[C:8]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:9]([OH:11])=[O:10].[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[C@@H:19](O)[CH2:18]2>CN(C)C=O.C(Cl)(Cl)Cl>[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[C@@H:19]([O:10][C:9](=[O:11])[C:8](=[O:7])[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[CH2:18]2

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 776942-Thiopheneglyoxylic acidHCID 914043-Quinuclidinol, (-)-

Product 1

HCID 44236097HCID 44236097, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent3×

Procedure

Oxalyl chloride (1.34 ml, 0.0154 mol) was added to a solution of oxothien-2-yl-acetic acid (2 g, 0.0128 mol) and dimethylformamide (one drop) in 30 ml of chloroform (ethanol free) at 0° C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolved in chloroform and evaporated again. This procedure was repeated two times. The product obtained was dissolved in CHCl3 (30 ml) and a solution of 3(R)-quinuclidinol (1.95 g, 0.0154 mol) in CHCl3 (30 ml) was added to this at 0° C. The mixture was stirred and allowed to warm at room temperature. After 1.5 h at r.t., the mixture was washed with 10% aqueous potassium carbonate, then with water, dried over Na2SO4 and evaporated to give 3.14 g (92.6%) of the title compound as a yellow oil. 1H-NMR (CDCl3): δ 1.40-1.50 (m, 1H), 1.50-1.70 (m, 1H), 1.70-1.80 (m, 1H), 1.90-2.0 (m, 1H), 2.15 (m, 1H), 2.70-3.05 (m, 5H), 3.30-3.40 (m, 1H), 5.05 (m, 1H), 7.20 (m, 1H), 7.85 (m, 1H), 8.10 (m, 1H).

Workup

  1. customAfter one hour the solvent was evaporated
  2. dissolutionThe residue was dissolved in chloroform
  3. customevaporated again
  4. customThe product obtained
  5. stirringThe mixture was stirred
  6. temperatureto warm at room temperature
  7. washthe mixture was washed with 10% aqueous potassium carbonate
  8. dry with materialwith water, dried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-dee92e5a3bd247d7a3564c3adec4dda9
Source dataset
uspto-grants-2014_08
Patent number
US08802699B2

Reaction notes

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