Methyl iodide → 2(3H)-benzoxazolone, 3-methyl-5-nitro-

HRID 2096818Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:16]I>CN(C=O)C>[CH3:16][N:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:11][C:10]1=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-nitro-3H-benzooxazol-2-one (26 g) in DMF (100 mL) was added to a suspension of NaH (60% in mineral oil, 10.71 g) in DMF (100 mL) over a period of 1 hour. Stirring was continued for 45 minutes at r.t. The mixture was cooled to 0° C. and methyl iodide dissolved in DMF (20 mL) was added dropwise over a period of 30 minutes. The mixture was stirred over night at r.t. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. CH2Cl2:methanol=4:1 (150 mL) was added to the resulting precipitate and the suspension was stirred for 1 hour at r.t. The solid was filtered off and dried in vacuo. The title compound was obtained as a orange solid (18.33 g, 62%). MS (EI)=194.0 [M+].

Workup

additionwas added dropwise over a period of 30 minutes
stirringThe mixture was stirred over night at r.t
extractionextracted two times with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was evaporated
additionCH2Cl2:methanol=4:1 (150 mL) was added to the resulting precipitate
stirringthe suspension was stirred for 1 hour at r.t
filtrationThe solid was filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-fc990cb5a7604e2c88ed8d1dda81889e
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450313B2

Reaction notes

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