SU1574590A1 - Method of obtaining mono and/or bis-2,7-octadienylformamide - Google Patents

Abstract

The invention relates to amides of carboxylic acids, in particular to the preparation of mono- and / or bis-2,7-octadienylformamide, which can be used to obtain biologically active substances and polymers. The purpose of the invention is to increase the yield of target products and simplify the process. The preparation is carried out by the reaction of butadiene with urea or ammonium bicarbonate in a formamide or dimethylformamide medium at 100-140 ° C in the presence of a catalyst that contains an equimolar amount of chloride, or palladium acetate or acetate (2+) and an organophosphorus compound f-ly PRb or P (OR) ₃ , where R2 is phenyl, butyl, R2 is phenyl. The method allows to obtain the desired products with a yield of up to 95% and simplify the process by increasing the processability of the process (using solid initial reagents), reducing the amount of the organophosphorus component of the catalyst. 1 tab.

Description

The invention relates to an improved process for the preparation of mono- (I) and / or bis-2,7-octadienyl s-II (II), which can be used to obtain biologically active substances and polymers.

The purpose of the invention is to increase the yield of the target product and simplify the process.

The invention is illustrated by examples (see table).

The general procedure for the preparation of formic acid 2,7-octadiyl amides is as follows.

In a steel autoclave (V 100 ml), 40 g (0.5 mol) of SdNSO3 or 30 g (0.5 mol) of NHeCONH, H g (0.5 mol) of HCO, 45 ml (0.5 mol) of butadiene are placed, then a catalyst consisting of 0.3 g of Pd (acac) j and 2.6 g of PPhe in 25 ml of DMF is added. Autoclaw is heated to 140 ° C and maintained for 20 hours with vigorous stirring. Chatham the reaction mass is cooled, -extracted with water (2 times 100 ml) to remove DMLA. The organic layer is extracted with benzene (2 x 50 ml)., The benzene extract of suiat NagRO / j, the benzene is distilled off.

four

receive products (T) and / or (TT). The distillation in vacuum is separated (I) and (tm).

N-2,7-oct dienyl Formamide (I); cml - 80 ° C 1 mm Hg, light yellow liquid with a weak odor, n 1.4910; IR spectrum (,): 915, 995, 3080 (CH-CKft), 970, 3030 (trans-), 1670 (NCHO), 3300 (NHJ. Spectrum (. E.): 1.41 m (2H, CH4 ), 1.98 m (4H,), 3.7 m (2H,), 4.91 m (2H,), 5.5 m (3N, CH-CH,), 7.08 s (1H.OCNH ), 8, .1 s (1H, NCOH). M 153.

N-2,7-bis-octadienyl-formamide (II) tKMn 180 & C (. Mm Hg n | ° 1.4910; IR spectrum (cm): 920, 980.1640,

the formation of solid starting reagents), reducing the amount of the organofluorine component of the catalyst.

Claims (1)

Invention Formula The method of obtaining mono- and / or bis- 2,7-octadienylformamide starting from thiene bujq in the presence of a catalyst containing a salt of divalent palladium and an organophosphorus compound, when heated in an organic solvent medium, is characterized by the fact that target products and process simplification, butadiene is reacted with urea or ammonium bicarbonate in Form 3030, 3080 (,), 1680 (Ouch). NMR4H spectrum ($, ppm): 1.7 m20 MFA or dimethylformamide at 100 (4H, -CH-), 2.1 m (8H,) 3.8 m140 0, with the use of catalysis 4H, C-SNL -), 4.8–5.6 m (YUN, torus, equimolar amount of CH,).% Of chloride, or acetate, or atomic method allows in palladium palladium, and LosAororggatch target products with a yield of up to 25 The logical compound of Lormula is PRI- or 95% and the process is simplified by the use of -P (OR), where R is phenyl, butyl: R1 Vydeleni its manufacturability (used-phenyl. 15745904 the formation of solid starting reagents), reducing the amount of the organofluorine component of the catalyst. Invention Formula The method of obtaining mono- and / or bis- 2,7-octadienylformamide starting from butadiene in the presence of a catalyst containing a salt of divalent palladium and an organophosphorus compound, when heated in an organic solvent medium, is also distinguished by the fact that in order to increase the yield of the target products and simplify the process, butadiene is reacted with urea or ammonium bicarbonate in medium. one l I one I 3 five eleven Butadiene MIH4S04: H „0 Illll Butadiene: NHtliro, II tn 1: lll Kutalien: Moscow: 1150 1: 1: 1 Booth diene urea: PDO 1: 1: 1 Vutadia: oath: H O 1: 1: 1 Butpdnen-urea: P, p 3: 1: 1 Wootddy EC: Urea: 117 (1 1: 1: 1 Woot diene: urine inp: hftO 5: 1: 1 Butadiene: urinary disease: H (, O 1: 1: 1 Vutadiene: urine ina: MgO 1: 1: 1 Formmund 1 GO2095, 7-octadienyl “Kormamnd (I LIFAILO-2060 Mixture 2,7-octadienylformamide (1.11) 1070 LMM1402098 J.Ch1-2, 7-Lys-octadieuyl. Norms | d (II) Lormamnd 1402090 Mixture of 2.7-octadiecylformamides (1.11) 55:45 DMLD 140 20 80 N, N -2 , 7-Yis-octadienne-formamide (II) LMMAI 101560Similarly LMFA1401545 A mixture of 2,7-octalne-alkylformads (I, II) LMFA1201634The same LM A1402095 K, K1 -2,7-bis-octadium | shlformeknd (II) №W A1002090To heh