Water → N-t-butoxycarbonyl-N-methyl-5-methoxy-2-nitroaniline

HRID 1061128Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].S(OC)(O[CH3:26])(=O)=O.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:19])[N:7]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])[CH3:26])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution at 0° C. of N-(5-methoxy-2-nitrophenyl)carbamic acid t-butyl ester (5.5 g) in dimethylformamide (35 ml) was added sodium hydride (0.9 g, 60% dispersion in mineral oil) and the mixture was stirred at 0° C. for 1 hour. A solution of dimethyl sulfate (2.2 ml) in dimethylformamide (5.5 ml) was slowly added dropwise at 0° C. and the mixture was stirred at the same temperature for 0.5 hours. At the end of this time, to the reaction mixture was slowly added water (55 ml) and the mixture was extracted with toluene (66 ml). The extract was washed with water and concentrated in vacuo to give the desired compound (5.8 g, yield 100%).

Workup

stirringthe mixture was stirred at the same temperature for 0.5 hours
extractionthe mixture was extracted with toluene (66 ml)
washThe extract was washed with water
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-81eacc3fdc8f4040a8b0b822164ac0c0
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525220B2

Reaction notes

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