N-Benzylideneaniline → N-(4-Chlorophenyl)-N-phenyl-benzenemethanamine

HRID 1086015

反応式

HRID 1086015 の反応式
[Cl:1]C1C=CC(OCC2C=CC=CC=2)=CC=1.C1(C=NC2C=CC=CC=2)C=CC=CC=1.[CH2:30]([N:37]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[Cl:1][C:47]1[CH:48]=[CH:49][C:44]([N:37]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:45][CH:46]=1

参加物

4

反応物 3

HCID 10858N-BenzylideneanilineHCID 69080BenzyldiphenylamineHCID 139062Benzene, 1-chloro-4-(phenylmethoxy)-

生成物 1

HCID 12229151N-(4-Chlorophenyl)-N-phenyl-benzenemethanamine

実験手順

Chloro-4-(phenylmethoxy)benzene (2.18 g, 0.010 mol) and N-(phenylmethylene)benzenamine (1.81 g, 0.010 mol) were reacted in Na/DMF (1 g: 50 mL) at 50° C. for 7 hrs. The reaction was followed by HPLC to about 90% conversion. This technique indicated among other things the presence of the title compound, benzyldiphenylamine, and some unknown material in a ratio 65:18:17. Similar aqueous workup as for the preparation of benzyldiphenylamine and chromatography on silica gave 0.50 g of the title compound mp 94-5° C. from methanol (lit mp 97-7.5° C. 70% yield. This material is contaminated with a small amount of diphenylbenzylamine. 1H NMR (200 MHz, CDCl3)δ (assignment): 5.03 (s, 2H, Ph2NCH2Ph), 6.96-7.38 (m, 14H, aromatic). MS [m/e (70 eV, % of base peak)] C19H16ClN 293 (M+., 52.8), 295 (M+. +2, 28.8), 202 (M+. --C7H7+, 22), 167 (C6H4NPh)+., 48.3), 91 (C7H7+, 100). FTIR (CDCl3): 3066, 3033, 1589, 1494, 1454 cm-1.

出典と根拠

ORDレコード
ord-8287c9582fbe465dbb688030f36dbb62
出典データセット
uspto-grants-1991_04
特許番号
US05011998

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