Claims
- 1. The process for preparing ortho-methyl anilines which comprises:
- (a) reacting an ortho-amino benzyl sulfoxide with a nonoxidizing acid halide in an inert solvent to produce a solution of the corresponding ortho-amio benzyl halide and sulfur by-products;
- (b) adding to the solution containing said ortho-amino benzyl halide and sulfur by-products a basic tertiary amine to form a quaternary ortho-amino benzyl ammonium halide salt;
- (c) precipitating said quaternary salt while retaining the sulfur compounds in solution; and
- (d) cleaving said quaternary salt by catalytic hydrogenation to form an ortho-methyl aniline.
- 2. The process of claim 1 wherein said starting sulfoxide is an ortho-methylsulfinylmethyl aniline.
- 3. The process of claim 1 wherein said starting sulfoxide is a 3-substituted-2-amino benzyl sulfoxide.
- 4. The process of claim 1 wherein said staring sulfoxide is a 3-trifluoromethyl-2-amino benzyl sulfoxide.
- 5. The process of claim 1 wherein said starting sulfoxide is 2-methylsulfinylmethyl-6-trifluoromethyl aniline.
- 6. The process of claim 1 wherein said acid halide is selected from the group consisting of acyl halides, haloacyl halides and inorganic acid halides.
- 7. The process of claim 6 wherein said acid halide is hydrogen halide.
- 8. The process of claim 1 wherein said tertiary amine is trimethyl amine.
- 9. The process of claim 1 wherein a solvent-co-solvent mixture is employed in step (d).
- 10. The process of claim 9 wherein said co-solvent is a lower alkyl alcohol.
- 11. The process of claim 10 wherein said co-solvent is methanol.
- 12. The process of claim 1 wherein a 3-trifluoromethyl-2-amino benzyl sulfoxide is reacted with hydrogen chloride in step (a) and trimethyl amine and methyl alcohol are employed in step (b).
- 13. The process of claim 1 wherein said solution of quaternary salt is seeded to aid crystallization.
- 14. The process of claim 1 wherein said ortho-amino benzyl sulfoxide is produced by in situ reaction of an ortho-amino benzyl sulfide with a halogenating agent to produce an aromatic cyclic sulfilimine intermediate which is rearranged by addition of water to ortho-amino benzyl sulfoxide.
- 15. The process of claim 1 wherein said ortho-amino benzyl sulfoxide is derived from a ortho-amino benzyl sulfide produced by an aniline sulfilimine rearrangement.
Parent Case Info
This is a division of application Ser. No. 358,773, filed Mar. 17, 1982, and now abandoned.
US Referenced Citations (2)
Non-Patent Literature Citations (2)
Entry |
Adams et al., "Organic Reactions", vol. 7, pp. 277-280 (1953). |
Grossman et al., "Tetrahedron Letters", vol. 6, pp. 497-500 (1922). |
Divisions (1)
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Number |
Date |
Country |
Parent |
358773 |
Mar 1982 |
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