p-Tetradecylaniline → 4-Tetradecylbenzenediazonium tetrafluoroborate

HRID 1365571Notes

Reaction equation

HRID 1365571 reaction equation
[CH2:1]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[F:22][B-:23]([F:26])([F:25])[F:24].[N:27]#[O+].[K+].[Br-]>C(#N)C.C(Cl)Cl>[F:22][B-:23]([F:26])([F:25])[F:24].[CH2:1]([C:15]1[CH:16]=[CH:17][C:18]([N+:19]#[N:27])=[CH:20][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 145224p-TetradecylanilineHCID 253877Potassium Bromide2×HCID 11137142Nitrilooxonium tetrafluoroborate

Product 1

HCID 448879534-Tetradecylbenzenediazonium tetrafluoroborateYield 69%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The 4-tetradecylaniline was dissolved in a 1:1 mixture of acetonitrile and dry methylene chloride prior to addition to the nitrosonium tetrafluoroborate. Yield: 69%. MP 82° C. IR (KBr) 3103.8, 2919.5, 2289.6, 1577.8, 1473.7, 1070.8, 1024.8, 844.5, 813.8, 716.9, 541.0, 510.2 cm−1. IR (KBr) 3103.8, 2919.5, 2289.6, 1577.8, 1473.7, 1070.8, 1024.8, 844.5, 813.8, 716.9, 541.0, 510.2 cm−1. 1H NMR (400 MHz, CDCl3) δ 8.02 (ABq, J=8.8 Hz, Δν=370.6 Hz, 4H), 2.76 (t, J=7.7 Hz, 2H), 1.61 (quin, J=7.8 Hz, 2H), 1.23 (s, 22H), 0.85 (t, J=7.0 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 159.92, 133.26, 131.94, 110.96, 37.49, 32.34, 30.87, 30.12, 30.10, 30.07, 30.04, 29.91, 29.78, 29.75, 29.72, 23.11, 14.55.

Sources & evidence

ORD record
ord-f68d16ca8340421692d499dc74c40f5f
Source dataset
uspto-grants-2011_02
Patent number
US07892517B2

Reaction notes

Loading…