Water → 2-Morpholino-5-nitrobenzo[d]oxazole

HRID 1896762Notes

Reaction equation

HRID 1896762 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=S)[NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.O>O1CCCC1>[O:17]1[CH2:18][CH2:19][N:14]([C:10]2[O:11][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:8]=3[N:9]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 7862935-Nitrobenzo[D]Oxazole-2-Thiol

Product 1

HCID 127114612-Morpholino-5-nitrobenzo[d]oxazoleYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-nitrobenzo[d]oxazole-2(3H)-thione (98.1 mg, 0.5 mmol) and morpholine (66 μL, 0.75 mmol) in tetrahydrofuran (3 mL) were heated at 150° C. for 15 min in the microwave. After cooling, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4 and absorbed on silica. Purification by column chromatography, eluting with ethyl acetate/hexanes 25:75 v/v affords 115 mg (92%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customabsorbed on silica
  6. customPurification by column chromatography
  7. washeluting with ethyl acetate/hexanes 25:75 v/v

Sources & evidence

ORD record
ord-b9875e7ba8904a2f9b073ed6e6475ae9
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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