Hydrochloric Acid → HCID 67242273, compound

HRID 729245Notes

Reaction equation

HRID 729245 reaction equation
[CH2:1]([NH:3][S:4]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])=[O:5])[CH3:2].CC(C)([O-])C.[K+].[C:20](OCC)(=[O:24])[C:21]([O-])=[O:22].Cl>C1COCC1>[CH2:1]([N:3]1[C:21](=[O:22])[C:20]([OH:24])=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4]1(=[O:5])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4467514N-ethyl-1-phenylmethanesulfonamideHCID 21943339Ethanedioic acid, monoethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 67242273HCID 67242273, compoundYield 2,754.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
145 °C

Procedure

N-Ethyl-1-phenylmethanesulfonamide (20 g) was divided into batches of 0.5 g each and taken in an 8 mL vial. To each vial was added potassium tert-butoxide (0.426 g, 3.8 mmol), ethyl oxalate (0.408 mL, 3.01 mmol) and dry THF (4 mL). Each vial was heated in a microwave reactor at 145° C. under pressure for 20 mins. Reaction mixture from all the vials were combined and treated with 1.5 N HCl (75 mL) and extracted with EtOAc. The organic layer was washed with water (3×25 mL) and brine, dried over Na2SO4 and evaporated. A small amount of the DCM was added to the solid residue and stirred well. Filtration gave nearly pure title compound (21 g, 82.6%) as off-white solid; 1H NMR (300 MHz, CDCl3) 1.47 (t, 3H, J=7.2 Hz), 3.8 (q, 2H, J=7.2 Hz), 7.3-7.5 (m, 3), 7.9-8.0 (m, 2H).

Workup

  1. customReaction mixture from all the vials
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water (3×25 mL) and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. additionA small amount of the DCM was added to the solid residue
  7. filtrationFiltration

Sources & evidence

ORD record
ord-9375fe79a6f840a5a05a7e379dc4229b
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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