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US 2007/0191638 A1Published application
Processes for the synthesis of N,N'-substituted 1,3-diketimines
OwnerKyung-Ho Parkinventor
Life of this patent
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Abstract
Processes for the synthesis of N,N′-substituted 1,3-diketimines (III) from the reaction of aliphatic ketimines with iminothioethers in the presence of base are provided. The processes are particularly useful for making aliphatic N,N′-unsymmetrically substituted 1,3-diketimines.
Claims8
A process comprising:
- a. reacting R3N═C(R1)CH2R5 with an alkali metal or alkaline earth metal base in a polar aprotic solvent to form a metalloenamine, [R3NC(R1)CHR5]−M+, where M is an alkali metal or an alkaline earth metal;
- b. reacting the metalloenamine with R6SC(R2)═NR4 to form a 1,3-diketiminate salt;
- and
- c. treating the diketiminate salt with a protic solvent to form a 1,3-diketimine, R3N═C(R1)C (R5)═C(R2)NHR4,
- wherein
- R1 is selected from the group consisting of C1-C5 linear alkyl groups and C6-C12 aryl groups;
- and
- R3 and R5 are independently selected from the group consisting of hydrogen, C1-C5 linear alkyl groups and C6-C12 aryl groups;
- or
- (R1, R3) or (R1, R5) taken together are (CR7R8)m, where R7 and R8 are independently selected from the group consisting of hydrogen and C1-C5 alkyl, and m is 3, 4 or 5;
- R2 and R4 are independently selected from the group consisting of hydrogen and C1-C5 alkyl groups and C6-C12 aryl groups;
- or
- (R2, R4) taken together are (CR9R10)n, where R9 and R10 are independently selected from the group consisting of hydrogen and C1-C5 alkyl, and n is 3, 4 or 5;
- and
- R6 is selected from a group consisting of C1-C10 alkyl and C6-C10 aryl groups.
12 more elements
Dependencies are inferred from the claim text.