Dimethyl Sulfoxide → 4-Methyl-6-nitro-2H-1,4-benzoxazin-3-one

HRID 1534979Notes

Reaction equation

HRID 1534979 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1)([O-:3])=[O:2].[CH3:15]S(C)=O>>[CH3:15][N:9]1[C:8]2[CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:12][CH2:11][C:10]1=[O:13]

Participants

3

Reactant 2

HCID 679Dimethyl Sulfoxide2×HCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 14777644-Methyl-6-nitro-2H-1,4-benzoxazin-3-one

Procedure

The title compound was prepared from 6-nitro-3-oxo-3,4-dihydro-(2H)-1,4-benzoxazine using the method described in Example 19. Yield: 3.01 g (56%) of product as a yellow solid. mp 185-187; 'H NMR (300 MHz, DMSO) and 7.968 (dd, J=8.9 Hz, 2H), 7.78 (d, J=2.5H 1H), 7.363 (d, J=8.9 2H), 4.799 (s, 2H), 3.32 (s, 3H); 13C NMR (75 MHz, DMSO) and 164.430, 144.77, 135.913, 118.824, 115.808, 111.5142, 66.944, 20.82; Mass Spectrum M+ m/z 208.

Sources & evidence

ORD record
ord-a151336d43ad42afbcc4095b4386c610
Source dataset
uspto-grants-1992_02
Patent number
US05091528

Reaction notes

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