tert-Butyl N,N-dipropan-2-ylcarbamimidate → N-(2-tert-butoxyethyl)-3-chloro-4-fluoroaniline

HRID 896259Notes

Reaction equation

HRID 896259 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([Cl:12])[CH:6]=1.C(N(C(C)C)C(=N)O[C:19]([CH3:22])([CH3:21])[CH3:20])(C)C>C(Cl)Cl>[C:19]([O:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([Cl:12])[CH:6]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 22010542tert-Butyl N,N-dipropan-2-ylcarbamimidateHCID 22349678N-2-hydroxyethyl-3-chloro-4-fluoroaniline

Product 1

HCID 22349667N-(2-tert-butoxyethyl)-3-chloro-4-fluoroanilineYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-2-hydroxyethyl-3-chloro-4-fluoroaniline (1.48 g, 7.81 mmol) in CH2Cl2 (20 ml) was reacted with N,N-diisopropyl O-tert-butyl-isourea (6.25 g, 31.2 mmol) at room temperature over night. The product was purified by silicagel chromatography, Eluant, ether/petroleum ether 5/95, 10/90 to give title compound (1.15 g, 60%).

Workup

  1. customThe product was purified by silicagel chromatography, Eluant, ether/petroleum ether 5/95, 10/90

Sources & evidence

ORD record
ord-da7c244e2963435497e4d1643dda372e
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

Loading…