4-Methyl-2,6-dinitroaniline → HCID 10487280, compound

HRID 1857417Notes

Reaction equation

[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:4]([N+:12]([O-])=O)[CH:3]=1>C(O)C.O>[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:4]([NH2:12])[CH:3]=1

Participants

Conditions

Temperature: 28 °C

Procedure

The procedure of Gillespie et al., J. Org. Chem. 25:942 (1960) was adopted as follows. A dark black solution of 4-methyl-2,6-dinitroaniline (0.100 g, 0.561 mmol, Aldrich, used as received) in 6.66% aq. (NH4)2S (3.3 mL, prepared from 20% aq.(NH4)2S solution supplied by Aldrich) and ethanol (3.5 mL) was refluxed for 45 min. It was then cooled to 28° C. and the solvents were removed as much as possible under vacuum (inside the hood to avoid the stench of ammonium sulfide). The slurry so obtained was diluted with water (10 mL) and the resulting red solid was filtered and dried under vacuum to obtain 0.072 g (85%) solid as a red powder, which was used as such for the next reaction. 1H NMR (acetone-d6): 2.205 (s, 3H), 6.342 (br s, 2H), 6.622 (s, 1H), 7.571 (s, 1H).

Workup

customthe solvents were removed as much as possible under vacuum (inside the hood
customThe slurry so obtained
filtrationthe resulting red solid was filtered
customdried under vacuum

Sources & evidence

ORD record: ord-a63588a221a04c33a7d75e39ea6bdfca
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147075

Reaction notes

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