Benzofuran derivatives

• US 3,931,215 A
• Filed: 01/21/1974
• Issued: 01/06/1976
• Est. Priority Date: 01/26/1973
• Status: Expired due to Term

• Current Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Original Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Inventors: Rosch, Gunter, Schinzel, Erich, Sahm, Wilfried, Horn, Anton
• Primary Examiner(s): Winters, Sherman D.
• Application Number:
  US05/435,276
• Time in Patent Office: 715 Days
• Field of Search: 260/309.2
• US Class Current: 548/305.1
• CPC Class Codes: C07D 307/79 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
• CPC Class Codes: C07D 307/92 Naphthofurans; Hydrogenated naphthofurans
• CPC Class Codes: Y10S 8/927 Polyacrylonitrile fiber

Abstract

Novel benzofuran containing a benzimidazolyl group are obtained by reacting a benzofuran containing a carboxylic acid halide group with either an ortho-phenylene diamine or an ortho-nitro-aniline derivative, in the latter case reducing the nitro intermediate to the corresponding (aminophenyl)-amide and splitting off water by closing the imidazole ring. The products are optical brighteners, especially for acrylonitrile polymers.

Claims

1. A compound of the formula ##SPC8##

in which L, M, P and Q are hydrogen, halogen, lower alkyl, lower alkoxy or phenyl of L and M together or P and Q together are a cyclohexenyl or phenyl ring annellated at the positions 4 and 5;

U is hydrogen, lower alkyl or phenyl;

V is hydrogen, lower alkyl, benzyl, phenyl or phenyl substituted by chlorine, methyl or methoxy;

W is lower alkyl, cyanomethyl, carbamylmethyl, carboxymethyl, lower carboalkoxymethyl, benzyl or benzyl substituted in the phenyl moiety by chlorine, methyl of methoxy;

Y is a group of the formula ##SPC9##

n is zero or 1 and F is a colorless anion.

3. A compound as defined in claim 1, wherein L, M, P and Q are hydrogen, methyl or methoxy and L and M together and P and Q together are annellated phenyl at the positions 4 and 5;

U is hydrogen or methyl;

V is hydrogen or methyl;

W is methyl;

Y is a group of the formula ##SPC11##

n is zero or 1 and F is chloride or methosulfate.

4. The compound as claimed in claim 1, in which L, M, P, Q, U and V are hydrogen, Y is p-phenylene and n is zero.

5. The compound as claimed in claim 1, in which L, M, P, Q, and U are hydrogen, V is methyl, Y is p-phenylene and n is zero.

6. The compound as claimed in claim 1, in which L, M, P, Q and V are hydrogen, U is methyl, Y is p-phenylene and n is zero.

7. The compound as claimed in claim 1, in which L, M, P and Q are hydrogen, U and V are methyl, Y is p-phenylene and n is zero.

8. The compound as claimed in claim 1, in which P, Q and U are hydrogen, L is 5-methyl, M is 6-methyl, V is methyl, Y is p-phenylene and n is zero.

9. The compound as claimed in claim 1, in which P, Q and U are hydrogen, L is 5-methyl, M is 6-methyl, V and W are methyl, Y is p-phenylene, n is one and R is methosulfate.

10. The compound as claimed in claim 1, in which L, M, P and Q are hydrogen, U, V and W are methyl, Y is p-phenylene, n is one and F is methosulfate.

2. A compound of the formula ##SPC10##

in which L, M, P and and Q are hydrogen, chlorine, lower alkyl or lower alkoxy or L and M together or P and Q together are a cyclopentenyl, cyclohexenyl or phenyl ring annellated at the positions 4 and 5;

U is hydrogen or methyl;

V is hydrogen or methyl;

W is methyl or benzyl;

Y is phenylene or naphthylene;

n is zero or 1 and F is halogen, lower alkyl sulfate, lower alkysulfonate, phenylsulfonate or tosylate.