METHOD OF PREPARING SULTINES

• US 20110124883A1
• Filed: 01/27/2011
• Published: 05/26/2011
• Est. Priority Date: 08/01/2007
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Indusegaram, Sutharsiny, Vonwiller, Simone Charlotte, Ridley, Damon Donald
• Granted Patent: US 8,119,820 B2
• Time in Patent Office: Days
• US Class Current: 549/15
• CPC Class Codes: C09B 47/06 Preparation from carboxylic acids or derivatives thereof , e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
• CPC Class Codes: C09D 11/50 Sympathetic, colour changing or similar inks

Abstract

A method of preparing a sultine from a dihalogeno compound. The method comprises the steps of reacting the dihalogeno compound with a hydroxymethanesulfinate salt in a DMSO solvent so as to prepare the sultine.

Claims

1. A method of preparing a sultine of formula (V) from a dihalogeno compound of formula (IV)

2. The method of claim 1, wherein X is Cl or Br, and NaI is present.

3. The method of claim 1, wherein a metal carbonate base is present.

4. The method of claim 1, wherein said hydroxymethanesulfinate salt is sodium hydroxymethanesulfinate.

5. The method of claim 1, wherein R₁, R₂, R₃ and R₄ are all hydrogen.

6. The method of claim 1, wherein said preparation is performed on a scale of at least 0.3 moles of the dihalogeno compound (IV).

7. The method of claim 1, wherein said temperature is in the range of 50 to 100°

C.

8. The method of claim, further comprising the step of:

reacting said sultine (V) with maleic anhydride at elevated temperature to generate a naphthalic anhydride as a Diels-Alder adduct,

9. The method of claim 8, wherein said naphthalic anhydride is used as a precursor for naphthalocyanine synthesis.

10. The method of claim 9, wherein said naphthalocyanine synthesis proceeds via conversion of said naphthalic anhydride to a benzisoindolenine.

11. The method of claim 9, wherein R₁, R₂, R₃ and R₄ are each hydrogen.