Nitronium tetrafluoroborate → (4-Methoxy-7-nitro-benzooxazol-2-yl)-carbamic acid methyl ester

HRID 1611960Notes

Reaction equation

HRID 1611960 reaction equation
[CH3:1][O:2][C:3](=[O:16])[NH:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:8]=2[N:9]=1.F[B-](F)(F)F.[O:22]=[N+:23]=[O:24]>[N+](C)([O-])=O>[CH3:1][O:2][C:3](=[O:16])[NH:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([N+:23]([O-:24])=[O:22])=[C:10]([O:14][CH3:15])[C:8]=2[N:9]=1.[CH3:1][O:2][C:3](=[O:16])[NH:4][C:5]1[O:6][C:7]2[C:13]([N+:23]([O-:24])=[O:22])=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:8]=2[N:9]=1

Participants

5

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 23593639(4-Methoxy-benzooxazol-2-yl)-carbamic acid methyl ester

Product 2

HCID 23593644(4-Methoxy-7-nitro-benzooxazol-2-yl)-carbamic acid methyl esterYield 32%HCID 69288402(4-Methoxy-5-nitro-benzooxazol-2-yl)-carbamic acid methyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a stirred solution of 780 mg (3.51 mmol) (4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 40 ml nitromethane at 0° C. was added 699 mg (5.27 mmol) nitronium tetrafluoroborate and stirring continued for 18 h while the reaction mixture was allowed to warm gradually to room temperature. The mixture was then concentrated in vacuo. Flash chromatography (ethyl acetate/hexane) afforded 300 mg (32%) (4-methoxy-5-nitro-benzooxazol-2-yl)-carbamic acid methyl ester as an orange solid, and 220 mg (32%) (4-methoxy-7-nitro-benzooxazol-2-yl)-carbamic acid methyl ester as a yellow solid. ES-MS m/e (%): 268 (M+H+, 100).

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-6b4fcf2843f74fb381f44a0ad6a0a516
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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