1-Iodo-4-nitrobenzene → 4-(Diethylphosphoryl)aniline

HRID 1948001Notes

Reaction equation

HRID 1948001 reaction equation
[CH2:1]([P:4]([C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)N)([CH2:6][CH2:7]C)=[O:5])[CH2:2]C.C(P(=O)CC)C.IC1C=CC([N+:29]([O-])=O)=CC=1>>[CH2:1]([P:4]([C:9]1[CH:10]=[CH:11][C:13]([NH2:29])=[CH:14][CH:15]=1)([CH2:6][CH3:7])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 124951-Iodo-4-nitrobenzeneHCID 672552723-(Dipropylphosphoryl)aniline2×HCID 178477251HCID 178477251, compound

Product 1

HCID 210595824-(Diethylphosphoryl)aniline

Procedure

The title compound was prepared according to the procedures leading to 3-(dipropylphosphoryl)aniline (Compound 168C) starting with the commercially available diethyl phosphine oxide and 4-iodonitrobenzene. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.47 (dd, J=8.46, 10.48 Hz, 2H), 6.74 (dd, J=2.27, 8.59 Hz, 2H), 3.97 (br. s., 2H), 1.76-2.02 (m, 4H), 1.11 (td, J=7.71, 16.67 Hz, 6H); MS (ES+): m/z: 198.0939 [MH+]. HPLC: tR=0.83 min (UPLC TOF MS: polar—3 min).

Workup

  1. customHPLC: tR=0.83 min (UPLC TOF MS: polar—3 min)

Sources & evidence

ORD record
ord-debf633e756f430588d5ebaf3a473cf4
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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