Tetrahydrofuran → 2-Ethylsulfanyl-5-nitrobenzooxazole

HRID 601546Notes

Reaction equation

HRID 601546 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[S:12])[NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:16]1COC[CH2:17]1>ICC>[CH2:16]([S:12][C:10]1[O:11][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:8]=2[N:9]=1)[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 7862935-Nitrobenzo[D]Oxazole-2-Thiol

Product 1

HCID 574214952-Ethylsulfanyl-5-nitrobenzooxazoleYield 41%

Reagents, catalysts & solvents 1

HCID 6340IodoethaneCatalyst

Conditions

Temperature
0 °C

Procedure

Dissolve 5-Nitro-3H-benzooxazole-2-thione (10.58 g, 53.9 mmol) in anhydrous THF (300 mL). Cool the mixture to 0° C. in an ice bath. Add NaH (4.90 g, 60% dispersion in mineral oil) slowly. Stir the resulting mixture at 0° C. for 10 min. Add iodoethane (20.0 mL, 0.250 mmol) to the stirring mixture. Allow the mixture to warm to room temperature and stir overnight. Adsorb the reaction mixture onto silica gel and subject to flash column chromatography in 2 batches (330 g, 120 g columns, eluting with 10-50% ethyl acetate/n-hexane both times) to yield the desired product (4.93 g, 41%). 1H NMR (400 MHz, DMSO-d6): δ 8.47 (d, J=2.4 Hz, 1H), 8.23 (dd, J=9.2, 2.6 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H), 3.37 (q, J=6.8 Hz, 2H), 1.45 (t, J=7.6 Hz, 3H).

Workup

  1. temperatureAllow the mixture to warm to room temperature
  2. stirringstir overnight
  3. washeluting with 10-50% ethyl acetate/n-hexane both times)

Sources & evidence

ORD record
ord-47ff2f3263c041feb1cb74c47e9c7ecb
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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