Water → Benzenamine, 2-nitro-4-(4-nitrophenoxy)-

HRID 1294053Notes

Reaction equation

C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=O)C.[H-].[Na+].Cl[C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19]([CH:21]=1)[NH2:20].[OH2:25].CN(C=[O:30])C>>[N+:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:16]2[CH:15]=[CH:21][C:19]([NH2:20])=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[CH:7][CH:6]=1)([O-:30])=[O:25]

Participants

Reactant 5

HCID 962Water

HCID 1983Acetaminophen

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 742185-Chloro-2-nitroaniline

Product 1

HCID 12032722Benzenamine, 2-nitro-4-(4-nitrophenoxy)-Yield 96%

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-acetamidophenol (7.56 g, 50 mmol) in DMF (20 ml) was added 60% NaH (2.2 g) followed by 5-chloro-2-nitroaniline (9.06 g, 50 mmol). The mixture was heated to 120° C. overnight. After cooling, 800 ml of water was added and the resultant solid was collected by filtration. Desiccation in vacuo gave intermediate 1 as a brown solid (13.75 g, 96%): MS m/e 286 (M−1).

Workup

temperatureAfter cooling
filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record: ord-3d0c9390ea434b1e908e91bbf69b2a71
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238813B2

Reaction notes

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