Diethylamine → HCID 10331271, compound

HRID 1190913Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:3]=1[CH2:4]OS(C1C=CC(C)=CC=1)(=O)=O.[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24]>O1CCOCC1>[CH2:23]([N:25]([CH2:26][CH3:27])[CH2:4][C:3]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:2]=1[F:1])[CH3:24]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of toluene-4-sulfonic acid 2-fluoro-5-nitro-benzyl ester (0.696 g, 2.13 mmoles) in 1,4-dioxane (4 mL) was added TEA (0.45 mL, 3.20 mmoles) and diethylamine (0.33 mL, 3.21 mmoles). The reaction mixture was stirred for 8 h at 55° C., concentrated and purified by TLC (petroleum ether/AcOEt/NH4OH//8/2/0.2). The expected compound was obtained as a yellow oil (0.365 g, 76% yield). MALDI-TOF: m/z 227.1 [M+H]+. 1H NMR (300 MHz, CDCl3) δ8.44; (dd, J=6.3 Hz and 2.9 Hz, 1H), 8.12; (ddd, 4-CH, J=8.9 Hz, 2.9 Hz and 4.4 Hz, 1H), 7.15; (dd, J=8.9 Hz and 8.9 Hz, 1H), 3.67; (s, 2H), 2.58; (q, J=7.1 Hz, 4H), 1.08; (t, J=7.1 Hz, 6H). 13C NMR (75 MHz, CDCl3) δ126.7; (CH, d, J=6.9 Hz), 124.1; (CH, d, J=10.2 Hz), 115.9; (CH, d, J=24.6 Hz), 49.6; (CH2), 47.1; (CH2), 11.8; (CH3).

Workup

concentrationconcentrated
custompurified by TLC (petroleum ether/AcOEt/NH4OH//8/2/0.2)

Sources & evidence

ORD record: ord-d3ca1fec981e41898c31e6e9185b3140
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680095B2

Reaction notes

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