Benzene → HCID 19773852, compound

HRID 1614437Notes

Reaction equation

[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1(/[C:7](/[N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:6]\[C:5]2[CH:13]=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 241Benzene

HCID 6854Carbazole

Product 1

HCID 19773852HCID 19773852, compound

Procedure

N-Phenylbenzaldimine (1.35 g, 0.0075 mol) and 9-benzylcarbazole (1.29 g, 0.0077 mol) were heated at 75° C. for 30 min in dimethylformamide (dry), 50 mL, and potassium tert-butoxide (0.10 g, 0.00089 mol). Based on reversed-phase HPLC results, the reaction was complete after 3 min. Aqueous work-up as above and recrystallization of the precipitate frommethanol gave needles mp 160°-2° C. (81%). 1H NMR (200 MHz, CDCl3) δ (assignment): 6.85-7.09 (m, 2H, aromatic). MS [m/e (70 eV, % of base peak)] C26H19N 345 (M+.,100), 267 (M+. -PhH, 25.8), 178 PhCCPh+., 47.5), 167 (carbazole+., 63.6). HRMS (m/z) for C26H19N (M+.) calcd. 345.1517 found 345.1513. FTIR (CDCl3): 3083, 3064, 3027, 1624, 1598, 1493, 1479, 1450, 1384, 1335, 1314, 1232 cm-1. Analysis: calcd. for C26H19N: C 90.40, H 5.54, N 4.05%; found: C 90.25, H 5.66, N 4.20%.

Sources & evidence

ORD record: ord-c322d965c3d244f89465ce9cf7978ea3
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196606

Reaction notes

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