1,8-Diazabicyclo(5.4.0)undec-7-ene → Benzenesulfonamide

HRID 890890Notes

Reaction equation

HRID 890890 reaction equation
ClC1OC([C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=C(C2C=CC=CC=2)N=1.COC1(C2C=C(C=CC=2)CS)CCOCC1.C1CCN2C(=NCCC2)CC1>C1COCC1.C(OCC)(=O)C>[C:16]1([S:19]([NH2:22])(=[O:21])=[O:20])[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 222460994-(2-Chloro-4-phenyl-5-oxazolyl)benzenesulfonamideHCID 857104633-[Tetrahydro-(4-methoxy)pyran-4-yl]benzyl mercaptan

Product 1

HCID 7370Benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 4-[(2-chloro)-4-phenyloxazol-5-yl]benzenesulfonamide (0.21 g, 0.63 mmol) in 2 mL of anhydrous THF at 5° C. was added a solution of 3-[tetrahydro-(4-methoxy)pyran-4-yl]benzyl mercaptan (prepared as described in U.S. Pat. No. 5,424,320) (0.15 g, 0.63 mmol) and DBU (95 mg, 0.63 mmol) in 5 mL of THF while maintaining the temperature at 5° C. The reaction mixture was stirred for 1 h at 5° C. for 5 h at room temperature. The reaction mixture was diluted with 100 mL of ethyl acetate and washed with 1 N HCl (1×100 mL), saturated aqueous NaHCO3 (1×100 mL), brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The concentrated residue was purified by flash column chromatography on silica gel, eluting with 40% ethyl acetate in hexane, to give 0.19 g (56%) of 4-[2-[3-(3,4,5,6-tetrahydro-4-methoxypyran-4-yl)phenyl]methylthio]-4-phenyloxazol-5-yl]benzenesulfonamide as a white solid: m.p. 74.7–78.5° C. 1H NMR (CDCl3/300 MHz) δ 1.85–1.97 (m, 4H), 2.92 (s, 3H), 3.71–3.85 (m, 4H), 4.48 (s, 2H), 4.87 (s, 2H), 7.29–7.47 (m, 7H), 7.60–7.69 (m, 4H), 7.86–7.90 (m, 2H). HRMS calcd for C28H28N2O5S2 537.1518. Found 537.1516.

Workup

  1. customprepared
  2. washwashed with 1 N HCl (1×100 mL), saturated aqueous NaHCO3 (1×100 mL), brine (1×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrated residue was purified by flash column chromatography on silica gel
  7. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f11fa81283f24521a77337e56a4f2f57
Source dataset
uspto-grants-2006_02
Patent number
US06998415B2

Reaction notes

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