SU886736A3 - Method of preparing chloroacetanilides - Google Patents

Abstract

Novel chloracetanilides of the formula I <IMAGE> (wherein R1, R2 and R3 each represents H, C1-4-alkyl, halogen or F3C, R4 represents C1-6-alkyl and n is 1, 2 or 3) and their manufacture from chloroacetyl chloride and the appropriate sec-amine. The novel compounds of the formula I have both a herbicidal and a growth-regulating action, and accordingly may be made up with suitable carriers into herbicidal preparations and may be used for treating living plants and areas of land.

Description

(54) METHOD FOR OBTAINING CHLOROCETHANILES The invention relates to a method for the preparation of novel substances, specifically chloro acetanilides of the general formula Bj. c1Ha (1ng- (os1ngyNg) .III. i. (iociHaCii ,:: Bg where I / H, CH3,. C1; H, CHij, CjrHg; R cn, n i-s. with herbicidal action. The proposed compounds are compared The known method has a wider range of herbicidal action and does not depend on TlJ. IJ soil. The proposed method is based on the known reactions of aniline production of h-toluene sulfonic acid 23 and chlorine acetyl chloride in the presence of 3J bases, Use as an initial reagent of aniline resch shchir 1Hy.d.r, and y-toluenesulphonic acid derivatives of general formula. uH3-iOt-o-iHa-chii- (ouiit-tei) rt: (ffii where R, R, R, n have the above values, allows you to get new substances and improved properties. The purpose of the invention is to obtain new compounds , specifically chloroacetacidides of general formula 1.. The goal has been achieved (by the method of producing chloroacetanilides of general formula ii in which aniline is common

Compound

Si- (W, D-Dioxageptl) -2, B-diAvtilaiit, chlorosuvic acid

 (4- (3,6-Dioxo-octyl) -27 methyleneshd3 chloro- 5% acetic acid

.b-Dioxahep

 thyl) ailide chloroacetic acid L

, 6-Diethyl "H-.3,6-dioxaheptyl) -anilide}

chloro-acetic acid C., and C1NO17 2 Oe

tM- (3,6-Dioxaheptyl) -2-methylainic chloro-acetic acid

1 Dl (3, b-Dioxok) 2,6-d | y etnanyl dZ chloroacetic acid.

; 2,6-Diethnl K Sz, 6dS (Ksookt1sh} -anil d. Chloroacetic acid

T a b 1 c a I

Elementary analy

CalculatedJ Poluchenb, X 1

C 60.0960.42

H 7.40 8.01

Ц5250

N .4.67-4.87

C) 1G, 8312.99

6.1

C 60,0959,06

And 7,408.03

1.5108

N 4,675.18

C1 11.8312.41

C56,4657,51

67.3

H6.68. 7.4

1.5260

N5,165; SO

€ 113.0513.97

Sat2,2861,79

91.8

H7,998.20

1.5214,

H4,274.30

.С110,8111,16

C 58,6458,13

87.5

And 7,057,32

1.5212

N 4i905.19:

CM2.4112.34

C 61,, 83

93.7 N .7.71 7.74

1.5200 N, 4.46 4.53 C1 .U, 30 11.92

C63,2362,70

93.6

H8,258,29

1.5176

N4,104,19

C110.3710.63

C vudolmshm tavl "-L

2-Chlor-1- (3; b-dioxaheptyl-6-methi / anilnd of chloro-acetic acid

f2-Xnop-ff- (3,6-flKox heptyl) -6-methylancl x orucetic acid

., 6-ioxaoctyl) -2-mwnlanig leadz chloroacetic acid

 2,6-Dimetkl-Y- y / CH3, §, 9-triyokadv qiui) -chloride acetic acid

W

SHC

C53.9053.10

82.0

H6,336,52

1.5252

N4,194,42

С121,2121,60

94.3

.С52,5151,71

H.5,985,83

1.5315

N4,384,34

.С122,1422,80

C60,0959,06

96, b

H7,408.03

1.5092

N4,675,18

С111,8312,41

C59,3859,50

.85,8

H7,627,66

I-,

1.5208

 N4,074,54

S110,3111,34

80.7

.С61,3661,76

H8,138,46

1.5190

N3,774.05

CJ9.5310.3 G

C58.2658.71,

, 337.50

1,5200

Я4,254,55

C110.75II, ". 9

Compound

Total forna a

 2, b-Jhat ntn- (3, 6,9,12-tetraoxate tetradecyl) taclide3 chloroacetic acid:

NW-Chloro 3, 6-dnoxage 11 tnl) aiyl "w wopopYKcycnoft acid. .

 G5,6-Di "et1 mN Sz, 6,9,12-tetraoxatrdecnl) anilide chloroacetic acid cell

12,6-F1methyl- | M 3, 6,9-trioxag undecyE-anipid chloroacetic acid

2-Ztil-6-methyl-M-13, 6-di-. oxaheptyl) -anilnd of chloroacetic acid

Elementary analysis

Mr. Vychnsle about, I Received

.

C59.7 "59.60

89,

I8.03, 8; 02

1.5104

N3,49. 3.50

(18.82 9.94

C50,9950,78

0.10

H5,605,87

N4,58A, 87

, 1623.75

91.7

C58,8358,62

H7,808.06

N3.61 3.82

C) 9,149,82

C 60.4160.63

90.8.

H 7,898.47

,

1.5140

M 3.91 4.14

Ct 9.9110.50

C 61.2360.68

89.9

And 7,, 91

1.5225

N 4,464,53

Ct 11,3012,02

P

i: i p r e m e n a e. O means the absence of KaKoro-jm6o

impact; - destruction of plants.

886736

12

Table 2 Formula and gains Method of obtaining chloroacetate {of the general formula J. formula characterized by rieM such that; gt of the general formula 1J UHi Br. iodvergadot interaction with a compound of the general formula III

CHX9j z 2 cH2c: H2) t, -OR

where R ,, Rj, RI, n have the above values in the medium of boiling toluene at the ratio And 8867 5

1. US patent 3547620, cl. 71-118, ony6JmK. 1970.

2. Bksher K., Pearson N. Organic syntheses, M., Mir, 1963i p. 509511.

3. The patent of France No. 1339001, kp. A 01 K), published. 1963. 6 after which the compound was developed; the general formula U Bi «« - «4wiH, -dHtj), - oBj. ks. Ny is treated with chloroacetyl chloride in a medium of ethyl acetate at a temperature of 25 O C and a ratio of Uf: acetyl chloride; RID 1: 2 in the presence of potassium carbonate. Sources of information taken into account in the examination

Claims (1)

Claim A process for preparing hloratsotanilidov general formula 1 '1 ^ .Sn _z CH _z - (0 (HF _g (1H1) _n -ovz' ^ doeHadi ⁴ Bt where R ^ «H, CHi, VOS ^, C1; R» »H CH _3> WR ^ = CH ₃ , ED ?; , n = 1-3, characterized in that ^ aniline of the general formula 1J W uht 886736 16 'after which the resulting compound of General formula 1U Bi •. ‘<Η is treated with chloroacetylchloride in ethyl acetate at a temperature of 2530 ° C and a ratio of 1U: chloroacetylchloride • 1: 2 in the presence of potassium carbonate. I g ¹ - S ″ 2. iodine is reacted with a compound of general formula III Λ Λ. .