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Modification of polystyrene by Friedel-Crafts reaction with substituted halo ethyl benzenes and haloethylphenols to make supports for solid phase peptide synthesis

Assignee: Yeda Research and Development Co Ltd
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Filing: 1974-10-03
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Granted: 1976-08-10
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Expires: 1994-10-03
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Abstract

Abstract A process for producing reagents useful in organic synthesis, of the general formula ##SPC1## Wherein Z designates the ##EQU1## part of a polymeric backbone of a polymer like polystyrene, a copolymer comprising polystyrene and a comonomer like divinylbenzene, butadiene, and other copolymers comprising styrene, or wherein Z designates the aliphatic moiety of a long-chain aralkyl compound having a terminal phenyl moiety; n is an integer from 1 to 8, inclusive; R designates oxygen or sulfur; X designates nitro, carbonyl, carboxyl, cyano-carbalkoxy or a carboxamido group which may be substituted on the nitrogen atom, or a halogen atom, or alkyl, unsaturated alkyl, aralkyl; RH and X together designate hydroxytriazole; which comprises reacting a compound of the general formula ##SPC2## Wherein Y designates --Cl, --Br, or --OH and X and R are as defined above, with a polystyrene polymer or with a copolymer as defined above, or with a long-chain araliphatic compound as defined above, in a Friedel-Crafts reaction. According to a preferred embodiment copolymers of polystyrene and divinylbenzene are used. The invention also relates to the novel products obtained by the above reaction.

Inventors

  • 👤 Abraham Patchornik
  • 👤 Rami Kalir
  • 👤 Matityahu Fridkin
  • 👤 Abraham Warshavsky

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 18:06
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/02; C08F8/10

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 88 words
A process for producing reagents useful for effecting reactions of organic synthesis, of the general formula ##SPC11## wherein Z designates the ##EQU2## part of a polymeric backbone of a polymer like polystyrene, a copolymer comprising polystyrene and a comonomer like divinylbenzene, butadiene and other copolymers comprising styrene; n is an integer from 1 to 8, inclusive; R designates oxygen or sulfur; X designates nitro, carbonyl, carboxyl, cyano-carbalkoxy or a carboxamido group which may be substituted on the nitrogen atom, or a halogen atom, or alkyl, unsaturated alkyl, aralkyl;
Claim 2
Dependent Claim 88 words
A process for producing reagents useful for effecting reactions of organic synthesis, of the general formula ##SPC11## wherein Z designates the ##EQU2## part of a polymeric backbone of a polymer like polystyrene, a copolymer comprising polystyrene and a comonomer like divinylbenzene, butadiene and other copolymers comprising styrene; n is an integer from 1 to 8, inclusive; R designates oxygen or sulfur; X designates nitro, carbonyl, carboxyl, cyano-carbalkoxy or a carboxamido group which may be substituted on the nitrogen atom, or a halogen atom, or alkyl, unsaturated alkyl, aralkyl;
Claim 3
Dependent Claim 45 words
or where RH and X together designate hydroxytriazole which comprises reacting a compound of the general formula ##SPC12## wherein Y designates --Cl, --Br, or --OH, and X and R are as defined above, with a polystyrene polymer or polystyrene containing copolymer in a Friedel-Crafts reaction.
Claim 4
Dependent Claim 45 words
or where RH and X together designate hydroxytriazole which comprises reacting a compound of the general formula ##SPC12## wherein Y designates --Cl, --Br, or --OH, and X and R are as defined above, with a polystyrene polymer or polystyrene containing copolymer in a Friedel-Crafts reaction.
Claim 5
Dependent Claim 18 words
A process according to claim 1, wherein the polymer is polystyrene or a copolymer of polystyrene and divinylbenzene.
Claim 6
Dependent Claim 17 words
A process according to claim 1, wherein the Y-(CH 2 ) n -group is a chloromethyl group.
Claim 7
Dependent Claim 43 words
A modification of the process according to claim 1, wherein the compound reacted with the polymer of the formula ##SPC13## and the product is of the general formula ##SPC14## wherein R, X, Z and n have the meaning as defined in claim 1.
Claim 8
Dependent Claim 23 words
A process according to claim 1, wherein the polymer is in the form of a gel-type, microreticular, macroreticular isoporous or popcorn type polymer.
Claim 9
Dependent Claim 13 words
A process according to claim 5, wherein the polymer is in bead form.
Claim 10
Dependent Claim 19 words
A process according to claim 5, wherein the polymer is in sheet form and the product is a membrane.

References Cited (Backward Citations)

US3645996A Cited
US3814732A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-08-10 1980-02-09 1980-08-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-08-10 1984-02-09 1984-08-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-08-10 1988-02-09 1988-08-10 $7700.00 Window Closed / Lapsed

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