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Method for preparation of an intermediate dye product

a technology of intermediate dye products and dye products, applied in the field of intermediate dye products, can solve the problems of ineconomic viability of the process

Inactive Publication Date: 2002-02-21
RES FOUND OF STATE UNIV OF NEW YORK THE STATE UNIV OF NEW YORK AT BUFFALO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0031] The formation of compound G can be avoided completely by converting the compound C to a mixture of enol ethers (compound D) by the careful addition of ethanol across one of the triple bonds of compound C to a mixture of enol ethers. That careful addition of ethanol across one of the triple bonds of compound C is an 0.07 M sodium ethoxide in ethanol. Addition of sodium sulfide or sodium hydrosulfide to the enol ethers, compound D, (both stereoisomers are observed in an 84:16 ratio) gives thiopyranone (compound E), if L is Sulfur, as the only heterocyclic product, which is isolated as a crystalline product from the crude reaction mixture.

Problems solved by technology

This process, however, is not economically viable because the overall yield of the critical compound (II) for the formation of compound (I) is below 30%, see synthesis example for compound (II) at columns 11 and 12 of the '475 patent.

Method used

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  • Method for preparation of an intermediate dye product
  • Method for preparation of an intermediate dye product
  • Method for preparation of an intermediate dye product

Examples

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Embodiment Construction

[0038] I. The following example of preparation of 2,6-di-tert-butylthiopyr-ylium pentamethine hexafluorophosphate dye, is presented for illustrative purposes and not meant to be restrictive.

[0039] Preparation of 1,5-Di-tert-butyl-1,4-pentadiyn-3-ol (Compound B).

[0040] Tert-Butylacetylene (41.0 grams, 0.500 mole) was dissolved in 1 L of dry tetrahydrofuran in a 5-L flask under an inert atmosphere of argon or nitrogen. The resulting solution was cooled to 0.degree. C. in an ice water bath. To the cold solution was slowly added 1.0 mole of a strong base to deprotonate the tert-butyl acetylene with stirring with the addition slow enough to maintain the temperature of the reaction mixture at or below 10 EC. Typically, either 200 mL of 2.5 M n-butyllithium in hexane (0.50 mole) or 167 mL of 3.0 M methylmagnesium bromide (0.50 mole) in ether gave identical results. After the slow addition of the base, the reaction mixture was stirred 1 hour at 0.degree. C. Methyl formate (16.5 grams, 0.275...

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Abstract

The present invention provides a novel method for the synthesis of an intermediate dye product having the following formula: wherein L is S, Te, or Se; R1 and R2 are either the same or different aryl or alkyl compounds; R3 is hydrogen or a short chain alkyl group; and Z is an anion. The process to formulate this intermediate compound entails reacting an R1-acetylene compound with an R2-acetylene compound (compounds A) into an enol ether compound with the R1 and / or R2 constituents (compound D) And from compound D, it forms into an intermediate dye compound having an L-based cyclic ring with the R1 and / or R2 constituents (compound F). With compound F the desired dye can be made with a greater overall yield for mass production.

Description

CLAIM OF PRIORITY[0001] This application claims priority to U.S. Provisional Patent application Ser. No. 60 / 214,190, filed on Jun. 26, 2000.[0002] The present invention relates generally to the field of dyes useful in image recording.DESCRIPTION OF RELATED ART[0003] Kawamura et al. in U.S. Pat. No. 4,283,475 discloses a 2,6-di-t-butyl-4-[5-(2,6-di-t-butyl-4H-thiopyran-4-ylidene)penta-1,3-dien-yl]thiopyrylium salts, and a process for production thereof. In particular, Kawamura et al. disclose 2,6-di-tert-butylthiopyrylium pentamethine hexafluorophosphate dye, as shown immediately below and identified as Compound (I), and variations of that dye. The variations alter the letter A from hydrogen to various other compounds disclosed in the '475 patent. 2[0004] The thiopyrylium pentamethine dye of compound (I) has properties that make it a useful laser dye. For example, it has an absorption maximum of 822 nm in dichloromethane. This wavelength is compatible with gallium-arsenide diode lase...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D335/02C07D345/00
CPCC07D335/02C07D345/00
Inventor DETTY, MICHAEL RAYVIRKLER, PETER ROBERT
Owner RES FOUND OF STATE UNIV OF NEW YORK THE STATE UNIV OF NEW YORK AT BUFFALO