SU435245A1 - METHOD OF OBTAINING S, 8-BIS- (TIOPHOSPHORIL) - p-MERCAPTOETHYLAMINES - Google Patents

Description

one

This invention relates to a process for the preparation of organophosphorus compounds, namely, new S, 8-bis- (thiophosphoryl) -p-mercaptoethylamines of general formula I

C1-A-0/0-A-C1

/ P-NHCH, CHvS-P

where A is alkylene;

R is alkyl or aryl.

These compounds can be used as physiologically active substances.

The process for the preparation of N, S-6Hc- (thiophosphoryl) p-mercaptoethylamines of general formula I consists in the reaction of bis- (thiophosphoryl) sulfide of general formula

CI-A-OV / 0-A-C1

/ P-s-f

JIS II il SR O Oh

where A and R are as defined above, with ethyleneimine.

The process is preferably carried out in an inert organic solvent, for example in benzene, at 15-50 ° C.

Target products are formed with virtually quantitative yield and are distinguished by known techniques. They are fluid, slightly mobile liquids.

Example 1. N, S-BHC- (O-p-chloroethyl-5-butyltnofosranl) -p-mercaptoethylamine.

To a solution of 0.02 mol of bis- (0-p-chloroethyl-5butylthiophosphoryl) sulfide in 25 ml of dry benzene, a solution of 0.02 mol of ethylenimine in benzene is added with stirring and cooling with ice water, maintaining the temperature in the reaction mass of 15-20 ° WITH. After adding ethyleneimine, the mixture is moved for another 2 hours at room temperature and 2 hours at 45-50 ° C, then the solvent is removed under reduced pressure to obtain the target substance in the form of a greenish slow-moving liquid. Quantitative output;

20

1.5305.

P

Found,%: N 2.68; R 12.11; S 18.74.

CiiHsiCbNO PaSa.

Calculated,%: N 2.77; P 12.25; S 19.00.

The following characteristic absorption regions (cm-) were found in the IR spectrum of the obtained compound: 540 (P-S-C), 610 (C-S), 670 (C-C1), 785 (C-S), 880 (P- N), 1030 (P-O-C), 1255 (P 0), 1475

(SNg-SNg-simm.), 2880-2980 (CH3-CH3-val.), 3265 (N-H-val.).

Example 2. N, S-BHC- (O-chloropropyl-5methylthiophosphoryl) -p-mercaptoethylamine.

This compound is prepared under the conditions of Example 1 from 0.02 mol of bis- (O-7-chloropropyl-5-methylthiophosphoryl) sulfide and 0.02 mol of ethylenimine. Quantitative output; 1.5430.

Found,%: N 3.17; P 13.61; S 21.90.

CioH23Cl2NO4P2S3.

Calculated,%: W 3,12; P 13.80; S 21.30.

C1-A-0

K.), SNg5-p (

RS

The following characteristic absorption regions (cm-) were found in the IR-spectrum of the obtained compound: 550 (P-S-C), 615 (C-S), 670 (C-Cl), 780 (C-S), 890 (P- N), 1035 (Р-О-С), 1250 (Р 0), 1310 (ЗСНз), 1440 (СН, -СН.; - Fmm.), 2880-2980 (СНг- -СН-shaft.), 3260 (N-N-shaft.).

Under the conditions of Example 1, other compounds are obtained, the list and analysis of which are presented in the table.