HU190515B - Process for producing sulfoximines - Google Patents

Abstract

The present invention is a process for preparing sulfoximines of the general formula I in which A is a methylene, vinylene or ethylene group optionally substituted by one or two alkyl groups each having 1 to 3 carbon atoms, B is a straight-chain or branched alkylene group having 2 to 6 carbon atoms and R 1 is an alkyl group having 1 to 3 carbon atoms optionally substituted by a phenyl group or a phenyl group, the phenyl nucleus being in each case represented by an alkyl group having 1 to 4 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a cyclohexyl, phenyl or halophenyl group, an alkyl group having 4 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a phenyl or disubstituted hydroxyphenyl di- or tri-substituted by alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 3 carbon atoms and / or halogen atoms - od the aminophenyl group, where the substituents of the phenyl nucleus may be identical or different, a naphthyl group optionally substituted by an alkoxy group having 1 to 3 carbon atoms or a pyridyl group, which is characterized in that of a compound of the general formula II in which A, B and R 1 are as defined above and R represents a hydrolytically cleavable acyl radical, the acyl radical is split off hydrolytically. The compounds of general formula I have valuable pharmacological properties, in particular antithrombotic effects. Formulas I and II

Description

The present invention relates to a process for the preparation of sulfoximines of general formula (I), which became known after the priority date of this application. The compounds have valuable pharmacological properties, in particular inhibiting thrombosis and tumor metastasis.

In the general formula (I)

Methylene, vinylene or ethylene optionally substituted with one or two C4-C3 alkyl groups,

B is a linear or branched C 2 -C 6 alkylene group; and

R 1 is C 1-3 alkyl optionally substituted with phenyl, or phenyl wherein the phenyl ring may be substituted with halo, C 1-4 alkyl, C 1-3 alkoxy, cyclohexyl, phenyl or halophenyl. C 1 -C 4 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 4 alkyl, C 1 -C 3 alkoxy, and / or halogen, or tri-substituted phenyl or disubstituted hydroxyphenyl or aminophenyl, and the substituents have the same or different meanings or a naphthyl group optionally substituted with C 1-3 alkoxy.

By R 1, halogen is understood to mean primarily fluorine, chlorine or bromine.

For example, among the above meanings for A, B, and R _t

Methylene, methylmethylene-dimethyl-methylene-diethyl-methylene, dipropyl-methylene-vinylene, methyl-vinylene or ethylene,

B is ethylene, η-propylene, η-butylene, n-pentylene, n-hexylene, 1-methylethylene, 2-methylethylene, 1-methyl-n-propylene, 2-methyl -n-propylene, 3-methyl-n-propylene, 1-methyl-n-butylene, 2-methyl-n-butylene, 3-methyl-n-butylene, 4-methyl-n-butylene, , 1-methyl-n-pentylene, 2-methyl-n-pentylene, 3-methyl-n-pentylene, 4-methyl-n-pentylene, 5-methyl-n-pentylene, 1,1- dimethyl ethylene, 1,2-dimethylethylene, 2,2-dimethylethylene, 1,1-dimethyl-n-propylene, 2,2-dimethyl-n-propylene, 3,3-dimethyl -n-propylene, 1,2-dimethyl-n-propylene, 1,1-dimethyl-n-butylene, 2,2-dimethyl-n-butylene, 3,3-dimethyl-n-butylene, 4,4-dimethyl-n-butylene, 1,2-dimethyl-n-butylene,

1,3-dimethyl-n-butylene, 1,4-dimethyl-n-butylene, 2,3-dimethyl-n-butylene, 1-ethyl-ethylene, 2-ethyl-ethylene, 1-ethyl -n-propylene, 2-ethyl-n-propylene, 3-ethyl-n-propylene, 1, ethyl-n-butylene, 2-ethyl-n-butylene, 3-ethyl-n-butylene, , 4-ethyl-n-butylene, 1-methyl-2-ethyl-ethylene, 1-methyl-2-ethyl-n-propylene, 1-methyl-3-ethyl-n-propylene, 1-methyl -2-propylethylene, 1-propylethylene, 1-butylethylene, or 1-propyl-n-propylene,

R1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, teicopentyl, hexyl, heptyl, benzyl, Ι-phenylethyl, , 2-phenylethyl, 1,1-phenylpropyl, 3-phenylpropyl, fluorobenzyl, chlorobenzyl, bromobenzyl, methylbenzyl, isopropylbenzyl, methoxy. benzyl, ethoxybenzyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, fluorophenyl, chlorophenyl, bromophenyl, methylphenyl, dimethylphenyl; , isopropylphenyl, tert-butylphenyl, methoxyphenyl, ethoxyphenyl, propoxyphenyl, cyclohexylphenyl, biphenyl, fluorophenylphenyl, chlorophenylphenyl, difluorophenyl, dichlorophenyl, dibromophenyl, dimethoxyphenyl, methoxychlorophenyl, methoxybromophenyl, methyl tert-butyl phenyl, methyl chlorophenyl, methyl bromophenyl, tert-butyl bromophenyl, dichloroaminophenyl, dibromoaminophenyl, dimethylaminophenyl, dichlorohydroxyphenyl, dibromohydroxyphenyl, dimethyl -hydroxyphenyl, di- (tert-butyl) hydroxyphenyl, trimethoxyphenyl, na denotes phthylmethoxynaphthyl.

Preferred compounds of formula I are those of formula I

A is dimethylmethylene, vinylene or ethylene, B is a straight chain C 3 -C 5 alkylene, and

R 1 is C 1-6 alkyl, phenylethyl, benzyl, e-cyclohexyl, naphthyl, methoxynaphthyl, or a C 1-4 alkyl group, methoxy, cyclohexyl, phenyl, fluorophenyl, fluorine; -, phenyl substituted with chlorine or bromine, phenyl substituted with C 1-4 alkyl or mephoxy, chlorine and / or bromine, and the substituents of the phenyl ring may be the same or different, or one, two chlorine or bromine atoms denotes aminophenyl, hydroxyphenyl or methoxyphenyl substituted with methoxy or two C 1 -C 4 alkyl groups. Particularly preferred are the compounds of formula I wherein

The dimethylmethylene, vinylene or ethylene group, the B n-butylene group and the

R 1 is methyl or methoxynaphthyl, or phenyl optionally substituted by methoxy, fluorine or chlorine, phenyl substituted by two chlorine or bromine atoms, phenyl substituted by two chlorine or bromine atoms, methyl bromophenyl, 4-arnino-3; , 5-dibromophenyl or di-tert-butyl) hydroxyphenyl.

According to the present invention, compounds of formula (I) are prepared by reacting compounds of formula (II): wherein A, B and R a are as defined above and R is a hydrolytically cleavable acyl group. - hydrolyze.

An example of an acyl group is a carboxylic acid or a carbonic acid derivative, such as an acetyl, propionyl, butancyl, benzoyl, pinanoyl, nicotinoyl, ethoxycarbonyl, aminocarbonyl or dimethylaminocarbonyl acyl.

Hydrolysis in the presence of an acid or base, for example, in the presence of hydrochloric acid, sulfuric acid, sodium hydroxide, potassium hydroxide or potassium carbonate, in a solvent or solvent mixture such as water, methanol, methanol, water ethanol or at temperatures ranging from 50 to 90 ° C.

The starting compounds of formula (II) are prepared according to methods known in the art, for example by reacting the appropriate hydroxy compounds with the appropriate halide in the presence of an aprotic solvent and an alkali metal base. The appropriate thioether is oxidized to form the halide required for the reaction, followed by reaction with 0-mesitylenesulfonylhydroxylamine, followed by acylation.

As mentioned above, the compounds of formula I have valuable pharmacological properties

They have primarily anti-thrombotic effects. They enhance the synthesis of Ij prostaglandin, an inhibitor of aggregation, and inhibit the metastatic spread of tumors.

The following examples illustrate the invention.

Example A

6- [4- (N-Acetyl-3,4-dichlorophenylsulfoximino) -butoxy] -3,4-dihydro-carbostyril

From 3,4-dichlorophenylsulfinyl-4-bromobutane and 0-mesitylene sulfonylhydroxylamine, 3,4-dichlorophenylsulfoximino-4-bromobutane is prepared, followed by 3,4-dichlorophenyl with acetic anhydride. - (N-acetylsulfoximino) -4-bromobutane.

M.p. 170-173 ° C. Yield: 98%.

163.2 (0.001 mol) of 6-hydroxycarbostyril was dissolved in 2 in 1 of dimethylsulfoxide, 448 mg (0.0013 mol) of 3,4-dichlorophenyl-N-acetylsulfoximino) -4-bromobutane and 27b, 3 mg. Anhydrous potassium carbonate (0.002 mol) was added and the reaction mixture was stirred for 17 hours at room temperature. Water is then added in small portions until the reaction product crystallizes in the form of white needles.

Melting point: 149-151 ° C. Yield: 267.1 mg (62.5%).

The following compounds were prepared analogously:

6- [4- (N-carbamoyl-3,4-dichlorophenylsulfoximino) butoxy] -3,4-dihydro-carbostyril, m.p. 148-150 ° C.

6- [4- (N-butyryl-3,4-dichlorophenylsulfoxynino) butoxy} ·

3.4-dihydrocarbostyril, m.p. 133135 ° C.

6- [4- (N-pivalol-3,4-dichloro-phenylsibifoximino) -butyl] -J-3,4-dihydro-carbostyril, m.p. 158160 ° C.

6- 4- [N- (2-methoxyacetyl> 3,4-dichlorophenylsulfoximino] butoxy-3,4-dihydrocarbostyril, m.p. 103-105 ° C.

6- [4- (N-benzoyl-3,4-dichloro-phenylsulfoximino) -butoxy] -3,4-dihydrocarbostyril, m.p. 110-111 ° C.

6- (4- [N- (4-methoxybenzoyl) -3,4-dichlorophenylsulfoximinol-butoxy-3,4-dihydro-carbostyril), m.p. 101-103 ° C.

6- [4-N-nicotinoyl-3,4-dichloro-phenylsulfoximino) -butoxy] -3,4-dihydro-carbostyril, m.p. 101103 ° C.

6- (4- [N- (2-Acetoxyphenylacetyl) -3,4-dichlorosulfoximino-butoxy-3,4-dihydrocarbostyril, Rf = 0.2 (silica gel plate, ethylene) chloride),

5- [4- (N-acetyl-3,4-dimethoxyphenylsulfoximino) butoxy] -3,3-dimethylindolin-2-one, Rf = 0.3 (hard gelatin plate, 9 : 1: ethylene chloride / ethanol),

5- [4- (N-Butyryl-3,4-dimethoxyphenylsulfoximino) butoxy] -3,3-dimethylindolin-2-one, Rf = 0.35 (silica gel plate, 1: 1: ethyl acetate / methylene chloride),

5- {4- (N-pivaloyl-3,4-dimethoxyphenylsulfoximino) butoxy] -3,3-dimethylindolin-2-one, Rf = 0.45 (silica gel plate, 1: 1: ethyl acetate / methylene chloride),

5- [4- (N-carbamoyl-3,4-dimethoxyphenylsulfoximino) butoxy] -3,3-dimethylindolin-2-one, Rf = 0.25 (silica gel plate, 9: 1 ratio ethylene chloride / ethanol),

5- [4- (N-dimethylaminocarbonyl-3,4-dimethoxyphenylsulfoximino) butoxy) -3,3-dimethylindolin-2-one,

Rf 0.3 (silica gel plate, 9: 1 ethylene chloride / ethanol),

5-4 [N- (4-chlorobenzoyl) -3,4-dimethoxyphenylsulfoximino-butoxy-3,3-dimethylindolin-2-one, m.p. 174-177 ° C.

5- [4- (1-glycotyroyl-3,4-dimethoxyphenylsulfoximino) -biotoxin-3,3-dimethylindolin-2-one, Rf = 0.25 (silica gel plate, 9: 1: ethylene chloride / ethanol '),

6- [4- (4-Benzoyl-4-fluorophenylsulfoximino) -butoxy] -4-dihydro-carbostyril, m.p. 64-68 ° C.

6- (4- [N- (4-chlorobenzoyl) -4-fluorophenylsulfoximino] butoxy] 3,4-dihydro-carbostyril, m.p. 134-138 ° C.

6- [4- (N-2-tenoyl-3,4-dichloro-phenylsulfoximino) -butoxy; -3,4-dihydro-carbostyril, m.p. 100-102 ° C.

6- [N-N - (*) - Pinanoyl-3,4- (chlorophenylsulfoxinino) butoxy] -3,4-dihydrocarbostyril, m.p.

- 74T,

6- [4- (N - (-) - Pinanoyl-3,4-dichlorophenylsulfoximino) -butyron-J-3,4-dihydrocarbostyril, m.p. 69-74 ° C.

6- [4- (N-acetyl-4-fluorophenylsulfoximino) butoxy] -3,4-d hydrocarbostyridine, Rf = 0.65 (silica, eluent: 85: 15 ethylene chloride / ethanol)

6- [4- (N-Butyryl-4-fluorophenylsulfoximino) -butoxy] -4- dihydrocarbostyril, Rf = 0.70 (silica, eluent: 85: 15 ethylene chloride / ethanol) )

6- [4- (N - (*) - Pinanoyl] -4-fluorophenylsulfoximino) butoxy-J-3,4-dihydrocarbostyril, m.p.

6- [4- (N) - (-) - Pinanoyl-4-fluorophenylsulfoxylmino) butoxy] -3,4-dihydrocarbostyril, m.p. 122-1.1 ° C.

Example 1

6- [4- (4-Fluorophenylsulfoxymino) butoxy] -3,4-dihydro-carbostyril

108 mg (0.0002 mol) of 6- [4- (N - (+) - pinoyloyl-4-fluorophenylsulfuximino) butoxy] -3,4-dihydrocarbostyril in 2 ml of 2N, 84.5% ethanol Aqueous ethanolic potassium hydroxide solution was heated at 80 ° C for 2 hours in an oil bath. It is neutralized with 5N hydrochloric acid, evaporated to dryness in vacuo, and the resulting dry salt is extracted with methylene chloride. The organic layer was dried over sodium sulfate, and the solvent was evaporated in vacuo and the residue was recrystallized from ethanol.

170-173 ° C. Yield: 64.5 mg (86%). Hydrolysis can also be carried out with 2.5N hydrochloric acid.

Example 2 t- [4- (3,4-Dichlorophenylsulfoxymethyl) butoxy] -3,4-dihydrocarbostyril

Prepared in analogy to Example 1 by hydrolysis of 6- [4- (N-acetyl-3,4-dichlorophenylsulfoxymethyl) -butoxy] -3,3,4-dihydrocarbostyril in methanolic potassium hydroxide. .

Melting point: 163-165 ° C. Yield: 89%.

Example 3

6- (4- (4-Fluorophenylsulfoximino) butoxy) -3.4 dihydrocarbostyril

That]. Prepared in an analogous manner to Example 1a by hydrolysis of 6- (4-N-benzoyl-4-fluorophenylsulfoximino) -buroxy) -3,4-dihydro-xrbostyril in ethanolic potassium hydroxide.

Melting point: 17O173 ° C. Yield. 88%.

Example 4

6. [4 ^ 4-fluoro-phenyl-sulfoximine> butoxy} carbostyril

Prepared in analogy to Example 1 by hydrolysis of 6- (4- (N-benzoyl-4-fluorophenylsulfoximino) butoxy) carbostyril in ethanolic potassium hydroxide.

176-178 ° C. Yield: 67%.

Example 5

5- (4- (3,4-Dimethoxyphenylsulfoximino) butoxy) 3,3-dimethylindolin-2-one

In a manner analogous to Example 1, 5- [4- (N-nicotinoyl-3,4-dimethoxyphenylsulfoximino) butoxy) -3,3-dimethylindolin-2-one was prepared in ethanolic potassium hydroxide. hidrolizásával.

Yield: 58%. Mp 107-109 ° C.

Infrared spectrum:

-CO-NH 3430 cm- ¹ = NH 3330 cm-1.

Example 6

5- (4- (3,4-Dimethoxyphenylsulfoximino) butoxy) -3,3-dimethylindolin-2-one

Prepared in analogy to Example 1 by hydrolysis of 5- (4- (N-acetyl-3,4-dimethoxyphenylsulfoximino) butoxy) -3,3-dimethylindolin-2-one with aqueous ethanol hydrochloric acid.

Melting point: 108-109 ° C. Yield: 83%.

Example 7

5- [4- (3,4-Dimethoxy-phenyl-sulfoximine) butoxy-3,3-dimethyl-indolin-2-one

In a manner analogous to Example 1, 5- [4- (N-carbamoyl-3,4-dimethoxyphenylsulfoximino) butoxy) -3,3-dimethylindolin-2-one was prepared in ethanolic potassium hydroxide. hydrolyzing.

Mp 107-108 ° C.

Hydrolysis may also be carried out with aqueous ethanol hydrochloric acid.

In analogy to the examples above, the following compounds may be prepared:

6- (4-phenylsulfoxyninobutoxy) 3,4-dihydro-carbostyril, m.p. 127-129 ° C.

6- [4- (4-tert-butyl-phenyl-sulfoximine) butoxy] -3,4-dihydro-carbostyril, mp: 20l-203 ^° C,

6- (4- (3,5-di-tert-butyl) -4-hydroxyphenylsulfoximino) butoxy} -3 4-dihydro-carbostyril, m.p.

110-112¾.

6- [4- (4-Cyclohexylphenylsulfoxylmino-butoxy) -3,4-dihydrocarbostyril, m.p. 174-176. 6- [4- (4-Biphenylsulfoximino) butoxy] -3,4-dihydrocarbostyril, m.p. 184-186. 6- [4- (Naphthyl- (2) sulfoximino) butoxy} -3,4-dihydro-carbostyril, m.p. <1,4-dihydrocarbostyril, m.p. 150-15-2,

6- [4- (3-Methyl-4-bromo-fetylsulfoxylamino) -butoxy} -3,4-dihydrocarbostyril, m.p. 150-152.

6- (4- (3,5-dibromo-4-aminophenylsilylphoximino) butyl] -1,3,4-dihydrocarbostyl, m.p. 110-113 ° C.

6- (4-phenylsulfoximino-butoxy) -carbosttril, m.p. 161-162 ° C.

6- [4- (4-tert-butylphenylsulfoximino) butoxy] carbosyril, m.p. 208-210 ° C.

6- [4- (3,5-Di- (tert-butyl) -4-hydroxyphenylsiliftoxyimino) rutoxybarbostyril, m.p. 205-207 ° C. carbostyril, m.p. 195-197 ° C,

6- [4- (4-biphenylylsulfoximino) butoxyl] carbostyril, m.p. 236-238 ° C.

6- (4-Cyclohexylsulfoximino-butoxy-carbostyl), m.p. 145-147 ° C, (4 (4-chlorophenylsulfoximino-butoxy-carbostyril, m.p. 201-203 ° C, m.p.

6- (4- (4-Bromo-phenylsulfoximino) -butoxy) -carbostyl> 1.1 mp 211-213 ° C;

6- (4- (3,4-dichlorophenylsulfoximino) butoxy] carboxide, m.p. 214-216 ° C.

6- (4- (3-Melyl-4-bromophenylsulfoximino) butoxy) -carbostol, m.p. 193-194 ° C.

6- (4- (2-fluoro-4-biphenylsulfoximino) butoxy) carboxyltyryl, m.p. 191-193 ° C.

6- [4- (3,5-Bromo-4-aminophenylsulfoximino) butoxy] carbostyril, m.p. 130-135 ° C.

3,3-dimethyl-5- [4- (4-methylphenylsulfoximino) butoxy} ndolin-2-one, m.p. 146-147 ° C.

3.3-methyl-5- (4- (4-tert-butyl-phenylsulfoximino) -butyl] -indolin-2-one, m.p. 195-197 ° C;

3.3-dimethyl-5- (4- (2-methyl-4-tert-butyl-phenylsulfoximiro} -butoxy) -indolin-2-one m.p.

3.3-Dimethyl-5- [4- (3,5-di-tert-butyl) -4-hydroxypentyl-sulfoxynino-butoxy] -indolm-2-one, Rf value:

0.25 (silica gel plate, eluent: 1: 1 ethyl acetate / methylene chloride),

3.3-Dimethyl-5- (4-cyclohexylphenylsulfoximino-butoxy)

ndolin-2one, m.p. 162-163 °.

3.3-dinethyl-5- [4- (2-naphthylsulfoximino) -butoxyl] -indo1-η-2-οη, m.p. 120-112 ° C,

3.3-dimethyl-5- (4-cyclohexylsulfoximino-butoxy) -irirolin-2-one, m.p.

3.3-dimethyl-5- (4-benzylsulfoximino-butoxy) -4-indolin-2-one, m.p. 98-99 ° C,

3.3 Dimethyl-5- [4- (4-fluorophenylsulfoximino} -butoxy} -indolin-2-one, m.p. 101-102.

3.3 Dimethyl-5- [4- (4-chloro-phenylsulfoximino) -butoxyl] -indolin-2-one, m.p. 136-1372.

3,3-dimethyl-5- [4- (4-bromophenylsulfoximino) butoxy] indolin-2-one, m.p. 160-161.

3.3-dimethyl-5- (4A (3,4-dichlorophenylsulfoximino) butoxybutyl] indolin-2-one, m.p. 147-148T,

3.3 Dimethyl-5- [4- (2,5-dichloro-phenylsulfoximino) -butyl] -indolin-2-one, Rf = 0.3 (silica gel plate, eluent: 1: 1) ethyl acetate / methylene chloride),

3.3-dimethyl-5- (4- (3-methyl-4-bromophenylsulfoxymethyl-butoxy) -indolin-2-one, m.p. 131-132 °.

3.3-dimethyl-5- [4- (2-fluoro-4-biphenylylsulfoxymethyl) butoxy] -indolin-2-one, m.p. 177-178 ° C.

3.3- dimethyl-5- [4- (3,5-dibromo-4-aminophenyl-szulfoxlmir o) butoxy] indolin-2-one, mp 202-204 C. ^c

190,515

3.3 Dimethyl-S- (4- (4-methoxymethylsulfoximino-4-butoxy) -indolin-2-one, m.p. 140-141 ° C.

3.3-dn.ethyl-5 {- (2-methoxyphenylsulfoximino) butoxy} · indolin-2-one, Rf = 0.35 (silica gel, ethyl acetate: 9: 1). chloride / ethanol);

3.3-dimethyl-5- [4- (6-methoxy-naphth-2-ylsulfoxino) butoxy] -indolin-2-one, m.p. 174-175 ° C.

3.3-dimethyl-5- (4-phenylsulfoximino-butoxy) -indolin-2-one, m.p. 111-112 ° C,

6- (4- (3,4-dimethoxyphenylsulfoximino) butoxy-3,4-dihydro-carbostyril, m.p. 154-156 ° C.

6- (3% 3,4-dichloro-phenylsulfanyl] foxitnino) propoxy] -3 _{d4-dihydro-carbostyril,} m.p. 144 -146 ^° C,

6- (5- (3,4-dichloro-phenyl sulfoximine) -pentoxil _4-3 4-dihydro-carbostyril, m.p. 154-155 ° C, ·, §

6- (3-ethylsulfoximinopropoxy) -3,4-dihydrocarbostyril, m.p. 107-109 ° C.

6- (3-ethylsulfoximino-propoxy) -carbostlyl, m.p. 166-167 ° C.

3.3-dimethyl-5- [4- (3,4-dimethyl-phenylsulfoximino) -butoxy] -indolin-2-one, m.p. 153-154 ° C.

3.3-dimethyl-5- (4-methylsulfoximino-butoxy) -indohn-2-one, m.p. 123-124 ° C;

6- (4-n-hexylsulfoximino-butoxy) -3,4-dihydro-carbostyril, m.p. 111-113 ° C.

6- (4- (2-phenyl-ethyl] -szulfoximino) butoxy] _-3-f 4-dihydro-carbostyril, m.p. 158-159 C. ^b, 25

5- (4-phenylsulfoximino-butoxy) -3,4-dihydrocarbostyril, m.p. 159-160 ° C.

7- (4-phenylsulfoxy) oximino-butoxy) -3,4-dihydrocarbostyril, m.p. 137-139 ° C.

8- (4-phenylsulfoximino-butoxy) -3,4-dihydrocarbostyril, m.p. 78-80 ° C.

Claims (4)

PATENT CLAIMS A process for the preparation of sulfoximines of the formula I in this formula Methylene, vinylene or ethylene optionally substituted with one or two C 1 -C 3 alkyl groups, B is a linear or branched C 2 -C 6 alkylene group; R1 represents a C1-C3 alkyl group optionally substituted by a phenyl group or a phenyl group wherein the phenyl ring may be substituted with a halogen atom, a C1-C4 alkyl group, a C1-C3 alkoxy group, a cyclohexyl, a phenyl or a halophenyl group. -C 7 -alkyl, C 3 -C 7 -cycloalkyl, C 1 -C 4 -alkyl, C 1 -C 3 -alkoxy, and / or phenyl or disubstituted hydroxyphenyl or aminophenyl substituted with halogen, and the same substituent on the phenyl ring is they may have different meanings or may be optionally substituted with C 1-3 alkoxy substituted naphthyl, characterized in that a compound of formula (II) has the following meaning: A compound of the formula wherein A, B and R 1 are as defined above and R is a hydrolytically cleavable acyl group, preferably pinanoyl, lower alkanoyl, benzoyl, nicotinod or aminocarbonyl group, the acyl group is cleaved by hydrolysis. Process according to claim 1, characterized in that the reaction is carried out in a solvent, preferably an aqueous solvent. The process according to claims 1 and 2, wherein the reaction is carried out in the presence of an acid or a base. 4. The process according to claims 1 to 4, wherein the reaction is carried out at a boiling point, preferably between 50 and 90 ° C.