Tetrahydrofuran → 2-Ethylsulfanyl-5-nitrobenzooxazole

HRID 1174924Notes

Reaction equation

HRID 1174924 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-2f6b9c423ecb4fee85f91e6a9c405226
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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