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US4419296A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of tertiary alkyl cyanides

Assignee: Bayer AG
•
Filing: 1982-03-02
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Granted: 1983-12-06
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Expires: 2002-03-02
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Abstract

Abstract Tertiary alkyl cyanides of the general formula ##STR1## wherein R 1 , R 2 and R 3 represent identical or different alkyl group or, together with the tertiary carbon atom to which they are bonded, form a polycycloalkyl group, or R 1 and R 2 , together with the tertiary carbon atom to which they are bonded, form a cycloalkyl group or a bicycloalkyl group, the alkyl groups, polycycloalkyl group, cycloalkyl group or bicycloalkyl group being optionally substituted by suitable substituents (as hereinbefore defined), are obtained in good yields by a process in which a tertiary alkyl halide of the formula ##STR2## wherein X represents a chlorine, bromine or iodine atom, and R 1 , R 2 and R 3 have the meaning given above, is reacted with trimethylsilyl cyanide of the formula, (CH 3 ) 3 SiCN (III), in the presence of a Lewis acid selected from SnCl 4 , TiCl 4 and BiCl 3 , and, if appropriate, in the presence of a diluent, at a temperature between 10° and 40° C. The tertiary alkyl cyanides of formula (I) can be used as intermediate products, for example for the preparation of known herbicides.

Inventors

  • 👤 Manfred T. Reetz
  • 👤 Ioannis Chatziiosifidis

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 05:47
CPC Classifications
C; C07; C07C; C07C255/00; C07C253/00; C07C253/14

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 125 words
A process for the preparation of a tertiary alkyl cyanide of the formula ##STR31## in which R 1 , R 2 and R 3 each independently is an alkyl group or, together with the tertiary carbon atom to which they are bonded, form a polycycloalkyl group, or R 1 and R 2 , together with the tertiary carbon atoms to which they are bonded, form a cycloalkyl group or a bicycloalkyl group, comprising reacting a tertiary alkyl halide of the formula ##STR32## in which X is a chlorine, bromine or iodine atom, with trimethylsilyl cyanide of the formula (CH 3 ) 3 SiCN in the presence of a Lewis acid selected from the group consisting of SnCl 4 , TiCl 4 and BiCl 3 .
Claim 2
Dependent Claim 125 words
A process for the preparation of a tertiary alkyl cyanide of the formula ##STR31## in which R 1 , R 2 and R 3 each independently is an alkyl group or, together with the tertiary carbon atom to which they are bonded, form a polycycloalkyl group, or R 1 and R 2 , together with the tertiary carbon atoms to which they are bonded, form a cycloalkyl group or a bicycloalkyl group, comprising reacting a tertiary alkyl halide of the formula ##STR32## in which X is a chlorine, bromine or iodine atom, with trimethylsilyl cyanide of the formula (CH 3 ) 3 SiCN in the presence of a Lewis acid selected from the group consisting of SnCl 4 , TiCl 4 and BiCl 3 .
Claim 3
Dependent Claim 21 words
A process according to claim 1, wherein the reaction is carried out at a temperature between about 10° and 40° C.
Claim 4
Dependent Claim 23 words
A process according to claim 1, wherein about 1 to 1.8 mols of trimethylsilyl cyanide are employed per mol of tertiary alkyl halide.
Claim 5
Dependent Claim 24 words
A process according to claim 1, wherein about 10 to 40 mol% of the Lewis acid is employed per mol of tertiary alkyl halide.
Claim 6
Dependent Claim 15 words
A process according to claim 1, wherein SnCl 4 is employed as the Lewis acid.
Claim 7
Dependent Claim 18 words
A process according to claim 1, wherein the reaction is carried out in the presence of a diluent.
Claim 8
Dependent Claim 22 words
A process according to claim 6, wherein the diluent is a chlorinated hydrocarbon free from chlorine bonded to a tertiary carbon atom.
Claim 9
Dependent Claim 15 words
A process according to claim 6, wherein dichloromethane or 1,2-dichloroethane is used as the diluent.
Claim 10
Dependent Claim 86 words
A process according to claim 1, in which R 1 , R 2 and R 3 each independently is an alkyl group having 1 to 10 carbon atoms, or, together with the tertiary carbon atoms to which they are bonded, form a polycycloalkyl group having up to 20 carbon atoms; or R 1 and R 2 together with the carbon atom to which they are bonded, form a cycloalkyl group having 3 to 12 carbon atoms or a bicycloalkyl group having 6 to 10 carbon atoms.
Claim 11
Dependent Claim 16 words
A process according to claim 1, wherein the tertiary alkyl halide is a tertiary alkyl chloride.
Claim 12
Dependent Claim 14 words
A process according to claim 1, wherein the tertiary alkyl halide is tert.-butyl chloride.
Claim 13
Dependent Claim 62 words
A process according to claim 11, wherein about 1.2 to 1.6 mols of trimethylsilyl cyanide and 20 to 30 mol % of the Lewis acid are employed per mol of tertiary alkyl halide, SnCl 4 is employed as the Lewis acid, and the reaction is carried out at about 15° to 25° C. in the presence of dichloromethane or 1,2-dichloroethane as diluent.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-12-05 1987-06-06 1987-12-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-12-05 1991-06-06 1991-12-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-12-05 1995-06-06 1995-12-06 $7700.00 Window Closed / Lapsed

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