Sodium hydride → HCID 178426797, compound

HRID 1385297Notes

Reaction equation

HRID 1385297 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:18][C:6]2=[C:7]([C:13]3[CH:17]=[CH:16][NH:15][N:14]=3)[S:8][C:9](S(C)=O)=[C:5]2[C:4](=[O:19])[CH2:3]1.[H-].[Na+].[CH:23]1([OH:27])[CH2:26][CH2:25][CH2:24]1>C1COCC1>[CH:23]1([O:27][C:9]2[S:8][C:7]([C:13]3[CH:17]=[CH:16][NH:15][N:14]=3)=[C:6]3[CH2:18][C:2]([CH3:20])([CH3:1])[CH2:3][C:4](=[O:19])[C:5]=23)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 178504628HCID 178504628, compound

Product 1

HCID 178426797HCID 178426797, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6,6-dimethyl-3-methanesulphinyl-1-(pyrazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (178 mg, 0.59 mmol) in cyclobutanol (1 mL) and THF (3 mL) was added sodium hydride (70 mg of a 60% dispersion in oil, 1.76 mmol). After effervescence had ceased the mixture was heated at 95° C. for 2h before the solvent was evaporated. The residue was partitioned between EtOAc (20 mL) and water (20 mL) and the organic layer separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol:EtOAc (1:1) to give the title compound (22 mg, 12%) as a pale yellow solid. mp 202-204° C. Found: C, 62.48; H, 6.24; N, 8.49%. C17H20N2O2S .0.5(H2O) requires: C, 62.74; H, 6.50; N, 8.61% 1H NMR (360 MHz, CDCl3) δ 1.06 (6H, s), 1.60-1.76 (1H, m), 1.86-1.97 (1H, m), 2.37 (2H, s), 2.38-2.47 (2H, m), 2.50-2.60 (2H, m), 2.79 (2H, s), 4.76 (1H, pentet, J=7.2 Hz), 6.45 (1H, d, J=2.4 Hz), 7.62 (1H, d, J=2.4 Hz). MS (ES+) 317 (M+1).

Workup

  1. customwas evaporated
  2. customThe residue was partitioned between EtOAc (20 mL) and water (20 mL)
  3. customthe organic layer separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with petrol:EtOAc (1:1)

Sources & evidence

ORD record
ord-00641151ee3c44e48d84476d045b9635
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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