4-Nitrobenzyl chloride → HCID 54015578, compound

HRID 1459620Notes

Reaction equation

[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1)([O-:24])=[O:23].[K+].[Br-]>>[OH:1][CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[N:15]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1

Participants

Reactant 3

HCID 74824-Nitrobenzyl chloride

HCID 253877Potassium Bromide

HCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 54015578HCID 54015578, compoundYield 89%

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by methods F and I, alkylating with 4-nitrobenzyl chloride, in 89% yield, mp 124°-127° C.; MS (Cl) MH+ 329; IR (KBr) 3498, 3076, 2930, 2863, 1656, 1605, 1500, 1466, 1302, 1279, 1184, 1126, 982, 613 cm-1 ; 1H NMR (CDCl3) δ 8.20 (dd, 2H, J=2.0, 6.9 Hz), 7.40 (d, 2H, J=8.8 Hz), 7.03 (m, 2H), 6.93 (m, 1H), 6.75 (d, 1H, J=7.6 Hz), 5.25 (s, 2H), 4.88 (dd, 1H, J=5.4, 7.6 Hz), 3.93 (m, 2H), 2.38-2.17 (m, 2H), 2.10 (m, 1H). Anal. Calc'd for C17H16 N2O5 : C 62.19, H 4.91, N 8.54. Found: C 62.05, H 4.87, N 8.39.

Sources & evidence

ORD record: ord-df3ab64a65ee4dec814ec02030167e47
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854242

Reaction notes

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