Hydrochloric Acid → HCID 67243180, compound

HRID 729243Notes

Reaction equation

HRID 729243 reaction equation
CC(C)([O-])C.[K+].[C:7]([NH:11][S:12]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])=[O:13])([CH3:10])([CH3:9])[CH3:8].[C:22](OCC)(=[O:28])[C:23](OCC)=[O:24].Cl>C1COCC1>[C:7]([N:11]1[C:23](=[O:24])[C:22]([OH:28])=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12]1(=[O:14])=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 562762N-tert-butyl-1-phenylmethanesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 67243180HCID 67243180, compoundYield 471.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

Potassium tert-butoxide (0.845 g, 10.56 mmol) was added to a solution of N-(tert-butyl)-1-phenylmethanesulfonamide (1.2 g, 5.28 mmol) and diethyl oxalate (0.85 mL, 6.33 mmol) in THF (8 mL) and the mixture was heated at 150° C. for 15 mins in a microwave reactor. The reaction mixture was acidified with 1M HCl, the THF was evaporated and the residue was extracted with DCM. The mixture was evaporated, the residue was triturated in petroleum ether and the solvent was decanted to give the title compound (7 g, 63%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.44-7.32 (m, 5H), 3.90 (br s, 1H), 1.36 (s, 9H); Mass Spectrum: M−H+280

Workup

  1. customthe THF was evaporated
  2. extractionthe residue was extracted with DCM
  3. customThe mixture was evaporated
  4. customthe residue was triturated in petroleum ether
  5. customthe solvent was decanted

Sources & evidence

ORD record
ord-c567e8fa42ad4663ad7a0baaf04387ee
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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