Hydrochloric Acid → HCID 68661688, compound

HRID 729252Notes

Reaction equation

HRID 729252 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([NH:9][S:10]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)(=[O:12])=[O:11])[CH3:8].[C:24](OCC)(=[O:30])[C:25](OCC)=[O:26].Cl>C1COCC1>[CH2:7]([N:9]1[C:25](=[O:26])[C:24]([OH:30])=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][CH:15]=2)[S:10]1(=[O:11])=[O:12])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 23665647Potassium tert-butoxideHCID 68662627N-ethyl-1-[4-(trifluoromethyl)phenyl]methanesulfonamide

Product 1

HCID 68661688HCID 68661688, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

Potassium tert-butoxide (0.309 g, 1.83 mmol) was added to a solution of N-ethyl-1-[4-(trifluoromethyl)phenyl]methanesulfonamide (0.49 g, 1.83 mmol) and diethyl oxalate (0.322 g, 2.20 mmol) in THF (4 mL) at 0° C. The mixture was heated in a microwave reactor at 150° C. for 10 mins. HCl (1M, 2 mL) was added dropwise to the mixture at 0° C. It was evaporated and the residue was extracted with DCM. The organic layer was dried and evaporated to give the title compound (0.480 g, 81%) as a solid; 1H NMR (500 MHz, CDCl3): δ 8.05 (d, 2H), 7.77 (d, 2H), 3.87 (q, 2H), 1.49 (t, 3H); Mass Spectrum: M−H+ 320.

Workup

  1. customIt was evaporated
  2. extractionthe residue was extracted with DCM
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-8cda38af14924b15933ff6035202f0db
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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