Nitric Acid → N,N-diethyl-4-(5-nitrothiazol-2-yl)aniline

HRID 56111Notes

Reaction equation

[CH2:1]([N:3]([CH2:15][CH3:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:2].[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[CH2:15]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][C:12]([N+:17]([O-:19])=[O:18])=[CH:13][N:14]=2)=[CH:8][CH:9]=1)[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of N,N-diethyl-4-(thiazol-2-yl)aniline (1.39 g, 6.00 mmol) and concentrated sulfuric acid (10 mL) was added concentrated nitric acid (0.45 mL) at −10° C. The reaction mixture was stirred at 0° C. for 3 h, then poured into ice water and extracted with CH2Cl2 (30 mL×3). The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=1:1) to give the title compound as a yellow solid (0.73 g, 44%).

Workup

extractionextracted with CH2Cl2 (30 mL×3)
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=1:1)

Sources & evidence

ORD record: ord-460b230015414682b9b604aca9f84f18
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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