3,5-Dichlorobenzyl chloride → HCID 54315739, compound

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.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([Cl:31])[CH:30]=1)[CH2:26]Cl.[K+].[Br-]>>[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([Cl:31])[CH:30]=1)[CH2:26][N:15]1[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12][CH:11]([CH2:10][CH2:9][OH:1])[C:16]1=[O:17]

Participants

Reactant 3

HCID 1378803,5-Dichlorobenzyl chloride

HCID 253877Potassium Bromide

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

Product 1

HCID 54315739HCID 54315739, compound

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 3,5-dichlorobenzyl chloride, in 89% overall yield. A sample was crystallized from CH2Cl2 /hexane/ether to afford a white solid, mp 104°-106° C.; IR (KBr) 3525, 1680, 1570, 1505, 1398, 1063, 760 cm-1 ; 1H NMR (CDCl3) δ 1.92 (br s, 1H), 2.17-2.37 (m, 2H), 3.93 (t, J=5.7 Hz, 2H), 4.87 (q, J=5.4 Hz, 1H), 5.13 (ABq, JAB =16.3 Hz, 2H), 6.78 (d, J=7.3 Hz, 1H), 6.93-7.05 (m, 2H), 7.12 (br d, J=1.7 Hz, 2H), 7.26-7.28 (m, 2H); Anal. Calc'd for C17H15Cl2NO3 : C, 57.97; H, 4.29; N, 3.98. Found: C, 57.96; H, 4.17; N, 3.87.