Acetic Acid → (2,6-Dimethyl-4-nitro-phenyl)-carbamic acid propyl ester

HRID 1820123Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of concentrated nitric acid (6.4 mL) in water (30 mL) was added (2,6-dimethyl-phenyl)-carbamic acid propyl ester (2.72 g), acetic acid (30 mL) and sodium nitrite (1.0 g). The reaction mixture was refluxed for 16 hours, water (200 mL) was added and the mixture was cooled to 0° C. The product was collected by filtration and dried in vacuo to furnish 1.40 g (42% yield) of the title compound as a yellow solid. The crude product was used without further purification. 1H NMR (500 MHz, DMSO-d6): 0.92 (t, 3H), 1.63 (m, 2H), 2.29 (s, 6H), 4.04 (t, 2H), 7.98 (s, 2H), 9.11 (b, 1H).

Workup

temperatureThe reaction mixture was refluxed for 16 hours
filtrationThe product was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-eb97b5415a45471a8301706c770fca96
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601870B2

Reaction notes

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