Sulfuric Acid → N-[1,1-dimethyl-3-[(2-nitrophenyl)amino]propyl]formamide

HRID 1095400Notes

Reaction equation

[CH3:1][C:2](O)([CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[CH3:3].C[Si]([C:21]#[N:22])(C)C.S(=O)(=O)(O)[OH:24].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]([NH:22][CH:21]=[O:24])([CH3:3])[CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2-methyl-4-[(2-nitrophenyl)amino]butan-2-ol (1.7 g, 7.8 mmol) and trimethylsilyl cyanide (4.2 mL, 31 mmol) was added concd. sulfuric acid at −30° C. and the mixture was warmed up to rt. After stirring for 24 h, the reaction mixture was cooled to 0° C. and to the mixture was added water and stirred for 30 min at rt. The mixture was poured into aq. potassium carbonate and extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with dichloromethane/methanol (25/1) to give 1.3 g (66%) of the title compound.

Workup

additionwas added concd
stirringstirred for 30 min at rt
extractionextracted with dichloromethane
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography on silica gel eluting with dichloromethane/methanol (25/1)

Sources & evidence

ORD record: ord-93b5bc2d63424a50bff5834c35b97214
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138177B2

Reaction notes

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