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US 5,179,207 AGranted
Substituted 2-amino-5-maleimido thiophenes and substituted 2-amino-maleimido thiazoles
AssigneeEastman Kodak Company
InventorsJames J. Krutak, Max A. Weaver
Life of this patent
Estimating the term…
Abstract
Provided are certain substituted 2-aminothiazoles and 2-aminothiophenes which are useful as red colorants and as intermediates in the synthesis of bathochromic azo dyes. These compounds are prepared by reacting 2-aminothiophenes or 2-aminothiazoles, which contain a primary amino group, with 2-chloro-3-negatively-substituted maleimides. These compounds can be diazotized and coupled with azo components, for example, anilines, 1,2,3,4-tetrahydroquinolines, 2,3-dihydroindoles, and 3,4-dihydro-2H-1,4-benzoxazines to form bathochromic blue-cyan azo dyes.
Claims9
A compound of the formula:
- ##STR36## wherein R is hydrogen;
- C.sub.1 -C.sub.8 alkyl;
- C.sub.1 -C.sub.8 alkyl substituted with at least one group selected from the list consisting of halo, hydroxy, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkanoyloxy , C.sub.5 -C.sub.7 cycloalkyl, cyano, C.sub.1 -C.sub.6 carbalkoxy, phenyl, phenyl substituted by one or two groups selected from the list consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy, phenoxy, phenoxy substituted with one or two groups selected from the list consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy, or R is C.sub.3 -C.sub.8 alkenyl;
- C.sub.3 -C.sub.8 alkynyl;
- C.sub. 5 -C.sub.7 cycloalkyl, C.sub.5 .C.sub.8 cycloalkyl substituted with one or two groups selected from the list consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, and C.sub.1 -C.sub.4 alkanoyloxy;
- phenyl;
- or phenyl substituted by one or two groups selected from the list consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy;
- X is cyano, C.sub.1 -C.sub.8 alkylsulfonyl, phenylsulfonyl, or phenylsulfonyl substituted by one or two groups selected from the list consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy;
- Y is hydrogen, C.sub.1 -C.sub.4 alkyl;
- C.sub.5 -C.sub.7 cycloalkyl;
- halogen;
- phenyl;
- phenyl substituted by one or two groups selected from the list consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy;
- 2-thienyl;
- 2-thienyl substituted with one of two halogen C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 alkoxy, or Y is 2-furanyl;
- Z is nitrogen or a group of the formula --C(R.sub.1) .dbd., wherein R.sub.1 is cyano, --CO.sub.2 R.sub.2, --COR.sub.3, --CONHR.sub.2, or --SO.sub.2 R.sub.3, wherein R.sub.2 is hydrogen;
- C.sub.1 -C.sub.8 alkyl;
- C.sub.1 -C.sub.8 alkyl substituted with at least one group selected from the list consisting of halo;
- hydroxy;
- C.sub.1 -C.sub.6 alkoxy;
- C.sub.1 -C.sub.6 alkanoyloxy;
- C.sub.5 -C.sub.7 cycloalkyl;
- cyano;
- C.sub.1 -C.sub.6 carbaloxy;
- phenyl;
- phenyl substituted by one or two groups selected from the list consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy, phenoxy;
- and phenoxy substituted with one or two groups selected from the listing consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy;
- or R.sub.2 is C.sub.5 -C.sub.7 cycloalkyl;
- C.sub.3 -C.sub.8 alkenyl;
- phenyl;
- or phenyl substituted by one or two groups selected from the list consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy;
- and R.sub.3 is C.sub.1 -C.sub.8 alkyl;
- phenyl;
- or phenyl substituted by one or two groups selected from the list consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.6 alkanoylamino, halo, cyano, C.sub.1 -C.sub.6 alkylsulfonyl, and hydroxy.
31 more elements
Dependencies are inferred from the claim text.