IP Library Granted Patent US 9,868,701
Granted Patent B2
US 9,868,701 · App. 15/539,059 · Granted Jan 16, 2018

Method for producing nitrogen-containing pentafluorosulfanylbenzene compound

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Quick Facts
Patent No.
US 9,868,701
App. No.
15/539,059
Granted
Jan 16, 2018
Kind
B2
Abstract

A method for producing a nitrogen-containing pentafluorosulfanylbenzene compound of formula (2a) or (2b): (wherein R 1 a hydrogen atom or a hydrocarbon group; Z is an aryl group linked to a carbonyl group; Y is a group of formula (Y1), (Y2), (Y3), or (Y4); R 2 is a hydrogen atom or a hydrocarbon group) the method comprising reacting a halogeno-pentafluorosulfanylbenzene compound of formula (1) with a nitrogenous nucleophile: (wherein X is a halogen atom; n is an integer of 1 to 5; R 1 is as defined above).

Claims (12)

1. A method for producing a nitrogen-containing pentafluorosulfanylbenzene compound of formula (2a) or (2b):

(wherein R 1 a hydrogen atom or a hydrocarbon group; Z is an aryl group linked to a carbonyl group; Y is a group of formula (Y1), (Y2), (Y3), or (Y4); R 2 is a hydrogen atom or a hydrocarbon group)

the method comprising reacting a halogeno-pentafluorosulfanylbenzene compound of formula (1) with a nitrogenous nucleophile:

(wherein X is a halogen atom; n is an integer of 1 to 5; R 1 is as defined above).

2. A method for producing a pentafluorosulfanylaniline compound of formula (3):

the method comprising reducing or hydrolyzing the nitrogen-containing pentafluorosulfanylbenzene compound as set forth in claim 1 .

3. The method according to claim 1 , wherein the nitrogenous nucleophile is at least one member selected from benzylamine compounds, hydrazine compounds, guanidine compounds, hydroxylamines and alkali metal salts of phthalimide.

4. The method according to claim 2 , wherein the reduction is carried out in the presence of hydrogen using Pd/C or Raney nickel as a catalyst.

5. The method according to claim 2 , wherein the hydrolysis is carried out using an aqueous acid solution or an aqueous alkali solution.

6. The method according to claim 1 , wherein an aprotic polar solvent is used as a solvent.

7. The method according to claim 6 , wherein the aprotic polar solvent is dimethyl sulfoxide or N-methyl-2-pyrrolidone.

8. The method according to claim 1 , wherein a base is used in the reaction of the halogeno-pentafluorosulfanylbenzene compound with the nitrogenous nucleophile.

Assignments (2)
CHANGE OF NAME Recorded Jul 14, 2023
From: UBE INDUSTRIES, LTD.
To: UBE CORPORATION
Reel/Frame 064275/0021 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 26, 2017
From: SHIMA, HIDETAKA; OMATA, YOUJI
To: UBE INDUSTRIES, LTD.
Reel/Frame 042818/0592 →