Oxalyl chloride → HCID 9908323, compound

HRID 1839177Notes

Reaction equation

HRID 1839177 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([S:14]([NH:17][C:18]2([C:24]([OH:26])=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:16])=[O:15])[CH:2]=1.C(Cl)(=O)C(Cl)=O.C(=O)(O)[O-].[Na+].Cl.[NH2:39][OH:40]>ClCCl.CN(C)C=O.O1CCCC1.O>[OH:40][NH:39][C:24]([C:18]1([NH:17][S:14]([C:3]2[CH:2]=[CH:1][C:9]3[C:8]4[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=4[O:6][C:5]=3[CH:4]=2)(=[O:16])=[O:15])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:26]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 9864315HCID 9864315, compound

Product 1

HCID 9908323HCID 9908323, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

1-(Dibenzofuran-3-sulfonylamino)-cyclohexanecarboxylic acid (0.18 g, 0.5 mmol) was dissolved in 50 mL dichloromethane with 2 drops of dimethylformamide. Oxalyl chloride (0.08 mL, 1.0 mmol) was added, and the resulting solution was stirred for 2 hours, then concentrated in vacuo. The resulting residue was dissolved in 10 mL tetrahydrofuran, and this solution was added dropwise to a mixture of sodium bicarbonate (0.61 g, 7.2 mmol) and hydroxylamine hydrochloride (0.33 g, 4.8 mmol) in 50 mL of a tetrahydrofuran/water mixture (1:1 ratio) that had been stirring for 10 minutes at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 64 hours. The reaction was concentrated in vacuo and partitioned between 1 M HCl and dichloromethane. The aqueous layer was extracted with additional dichloromethane, followed by drying the combined organic layers over magnesium sulfate, filtration, and concentration to give 0.07 g of an off-white solid, the structure of which is shown below. The compound had a melting point of about 184-186° C. 1HNMR (CDCl3): δ7.97 (d, 1H), 7.97 (s, 1H), 7.90 (dd, 2H), 7.75 (d, 1H), 7.48 (d, 1H), 7.41 (t, 1H), 7.27 (t, 1H), 6.65 (s, 1H), 1.79 (m, 4H), 1.14 (m, 6H) ppm. Analysis showed the compound to have an empirical formula of (C19H20N2O5S.0.25H2O).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in 10 mL tetrahydrofuran
  3. stirringhad been stirring for 10 minutes at 0° C
  4. stirringstirred for 64 hours
  5. concentrationThe reaction was concentrated in vacuo
  6. custompartitioned between 1 M HCl and dichloromethane
  7. extractionThe aqueous layer was extracted with additional dichloromethane
  8. customby drying the combined organic layers
  9. filtrationover magnesium sulfate, filtration, and concentration

Sources & evidence

ORD record
ord-fd1fe561ba1d423db8345e75a3fdc746
Source dataset
uspto-grants-2004_01
Patent number
US06677355B1

Reaction notes

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