Dinitrobenzonitrile → 2-((5-Methylisoxazol-3-yl)methoxy)-6-nitrobenzonitrile

HRID 471671Notes

Reaction equation

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

Participants

Reactant 2

HCID 520718Dinitrobenzonitrile

HCID 2736567(5-Methyl-1,2-oxazol-3-yl)methanol

Product 1

HCID 667459862-((5-Methylisoxazol-3-yl)methoxy)-6-nitrobenzonitrileYield 86%

Procedure

Prepared as in Example 187c from (5-methylisoxazol-3-yl)methanol and 2,6-dinitrobenzonitrile in 86% yield as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 2.43 (d, J=0.8 Hz, 3H), 5.50 (s, 2H), 6.38 (d, J=0.4 Hz, 1H), 7.83 (dd, J=1.2, 8.4 Hz, 1H), 7.91-7.98 (m, 2H). MS 260 (MH+).

Sources & evidence

ORD record: ord-95b628998677465caec51465c8b2f753
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633186B2

Reaction notes

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