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[ CAS No. 3567-62-2 ] {[proInfo.proName]}

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Chemical Structure| 3567-62-2
Chemical Structure| 3567-62-2
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Product Details of [ 3567-62-2 ]

CAS No. :3567-62-2 MDL No. :MFCD00088374
Formula : C8H8Cl2N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 219.07 Pubchem ID :-
Synonyms :

Safety of [ 3567-62-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3567-62-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3567-62-2 ]

[ 3567-62-2 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 102-36-3 ]
  • [ 74-89-5 ]
  • [ 3567-62-2 ]
  • [ 100961-22-6 ]
YieldReaction ConditionsOperation in experiment
With benzene
  • 2
  • [ 16240-18-9 ]
  • [ 3567-62-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
  • 3
  • [ 3567-62-2 ]
  • [ 372-09-8 ]
  • [ 126381-34-8 ]
YieldReaction ConditionsOperation in experiment
46% With acetic anhydride at 60℃; for 3h;
  • 4
  • [ 3567-62-2 ]
  • [ 298-12-4 ]
  • [ 134124-32-6 ]
  • [ 38655-54-8 ]
YieldReaction ConditionsOperation in experiment
In chloroform Heating;
  • 6
  • [ 330-54-1 ]
  • [ 34637-13-3 ]
  • [ 3567-62-2 ]
  • [ 69342-26-3 ]
  • [ 76409-92-2 ]
YieldReaction ConditionsOperation in experiment
With Fe(OH)(2+) In water for 4h; Photolysis;
YieldReaction ConditionsOperation in experiment
Bildung 1: O-Propionyl-N-methylcarbamoyl-N-(3-chlor-phenyl)-hydroxylamin, HCl;
Bildung 2: O-Acetyl-N-methylcarbamoyl-N-(3-chlor-phenyl)-hydroxylamin, HCl;
(yield)Bildung 1-2: 22percent;
Ester (2), 1) Δ, 2) 3,4-Dichloranilin;
Methylisocyanat, 3,4-Dichlor-anilin;
aus Methylisocyanat, 3,4-Dichlor-anilin;

  • 8
  • [ 3567-62-2 ]
  • [ 126381-37-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 46 percent / acetic anhydride / 3 h / 60 °C 2: 74 percent / 33 percent NaOH / 0.17 h / 80 °C
  • 9
  • [ 3567-62-2 ]
  • [ 126381-40-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 46 percent / acetic anhydride / 3 h / 60 °C 2: 63 percent / NaNO2 / H2O / 0.17 h / 95 °C
  • 10
  • [ 102-36-3 ]
  • [ 3567-62-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene 2: aq. HCl
  • 11
  • [ 1189-71-5 ]
  • [ 3567-62-2 ]
  • [ 80653-08-3 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; ethyl acetate; Petroleum ether 1 EXAMPLE 1 EXAMPLE 1 65.7 parts of N-methyl-N'-(3',4'-dichlorophenyl)-urea are suspended in 300 parts of dioxane. 42.5 parts of chlorosulfonyl isocyanate are added, a little at a time, at room temperature. After the mixture has been stirred for 16 hours, insoluble matter is filtered off and the solution is concentrated; residual solvent is removed at 40°-60° C./0.01 mbar. 90 parts of ethyl acetate are added to the residue and when the mixture has crystallized 200 ml of petroleum ether are added. The product is filtered off and dried, giving 75 parts of 2H-4-methyl-6-(3',4'-dichlorophenyl)-3,4,5,6-tetrahydro-1,2,4,6-thiatriazine-3,5-dione-1,1-dioxide (active ingredient 1), melting point 180°-183° C.
  • 12
  • 1-(3,4-dichlorophenyl)-3-(1-hydroxy-2,2,2-trichloroethyl)-3-methyl urea [ No CAS ]
  • [ 3567-62-2 ]
  • [ 75-87-6 ]
  • [ 39803-91-3 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In diethyl ether 3 Preparation of 1-methyl-1-(1,2,2,2-tetrachloroethyl)-3-(3,4-dichlorophenyl) urea EXAMPLE 3 Preparation of 1-methyl-1-(1,2,2,2-tetrachloroethyl)-3-(3,4-dichlorophenyl) urea 1-(3,4-dichlorophenyl)-3-methyl urea (15.2 g, 0.07 mol) was combined with 15.0 g (0.1 mol) of chloral and 5 drops of concentrated sulfuric acid. The mixture was heated for an hour to effect reaction, then stripped under vacuum. To the crude 1-(3,4-dichlorophenyl)-3-(1-hydroxy-2,2,2-trichloroethyl)-3-methyl urea was added an excess of thionyl chloride and the mixture was heated gradually to a maximum of 65° C. Diethyl ether was added to the crude product, and the insoluble product was collected on a filter, washed twice with diethyl ether and dried. The 15.3 g of product, which melted at 132°-140° C., analyzed as follows: %Cl, calculated 55.2, found 46.0.
  • 13
  • [ 75-76-3 ]
  • [ 3567-62-2 ]
  • [ 54892-17-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine; sulphur dichloride In dichloromethane 3 Example 3 Example 3 -- Preparation of N-chlorothio-N-methyl-N'-3,4-dichlorophenyl urea A 9.48-g (0.12 mol) sample of pyridine was added dropwise to a slurry of 21.9 (0.1 mol) N-methyl-N'-(3,4-dichlorophenyl) urea and 11.3 g (0.11 mol) sulfur dichloride in 100 ml methylene dichloride at 25°-30°C. After the completion of the addition, pyridine hydrochloride was filtered from the reaction mixture. The NMR spectrum of the reaction mixture showed a singlet at 3.5 ppm (relative to tetramethylsilane) for the N-methyl group of the N-chlorothio-N-methyl-N'-3,4-dichlorophenyl urea product.
  • 14
  • [ 624-83-9 ]
  • [ 95-76-1 ]
  • [ 3567-62-2 ]
YieldReaction ConditionsOperation in experiment
In di-isopropyl ether 4.A STEP A STEP A N-methyl-N'-(3,4-dichlorophenyl)-urea A mixture of 27.4 g of 3,4-dichloroaniline in 140 ml of isopropyl ether was added slowly to 9 g of methyl isocyanate in 100 ml of isopropyl ether and the mixture was refluxed for 2 hours and was then cooled to 0° C. The precipitate formed was recovered by vacuum filtration and was washed with isopropyl ether. The mother liquors were concentrated to obtain a second crop. The two combined crops weighing 19.5 g and melting at 156° C. were crystallized from ethyl acetate to obtain N-methyl-N'-(3,4-dichlorophenyl)-urea melting at 160° C., identical to the product described by Onley et al., J. Ass. Off. Anal. Chem., Vol. 52 (1969), p. 545. Analysis: C8 H8 Cl2 N2 O; molecular weight = 219.07; Calculated: %C, 43.86; %H, 3.68; %Cl, 32.37; %N, 12.79; Found: %C, 43.7; %H, 3.6; %Cl, 32.4; %N, 12.7.
  • 15
  • [ 5813-48-9 ]
  • [ 60-29-7 ]
  • [ 3567-62-2 ]
  • [ 41881-54-3 ]
YieldReaction ConditionsOperation in experiment
In pyridine 5 N-METHYL-METHYLTHIO-N'-(3,4-DICHLOROPHENYL)-UREA EXAMPLE 5 N-METHYL-METHYLTHIO-N'-(3,4-DICHLOROPHENYL)-UREA A mixture of 20 ml of methylsulfenyl chloride and 200ml of ethyl ether was added slowly while keeping the temperature below -30° C. to a solution of 40 g of N-methyl-N'-(3,4-dichlorophenyl)-urea in 500 ml of pyridine and the mixture was stirred for 1 hour at -30° C. After letting the temperature rise to 5° C., the mixture was stirred for 17 hours and the mixture was poured into a mixture of ice and water. The mixture was extracted with methylene chloride and the methylene chloride extract was washed with water and dried. The volatile fractions were removed by distillation under reduced pressure and the residue was crystallized from isopropyl ether to obtain 29.4 g of N-methyl-N-methylthio-N'-(3,4-dichlorophenyl)-urea melting at 93° C. A microanalytical sample was obtained by chromatography over silica gel and elution with a 9-1 benzene-ethyl acetate mixture. Analysis: C9 H10 Cl2 N2 OS; molecular weight = 265.16; Calculated: %C, 40.76; %H, 3.79; %Cl, 26.75; %N, 10.56; %S, 12.10; Found: %C, 40.6; %H, 3.8; %Cl, 26.8; %N, 10.5; %S, 12.0.
  • 16
  • [ 19760-03-3 ]
  • [ 3567-62-2 ]
  • [ 629-19-6 ]
  • [ 41881-66-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuryl dichloride In pyridine; dichloromethane; Petroleum ether 17 N-PROPYLTHIO-N-METHYL-N'-(3,4-DICHLOROPHENYL)-UREA EXAMPLE 17 N-PROPYLTHIO-N-METHYL-N'-(3,4-DICHLOROPHENYL)-UREA 13,4 g of sulfuryl chloride were slowly added at -30° C. to a mixture of 106 ml of methylene chloride and 15 g of dipropyldisulfide, and after the temperature rose to -10°C., the mixture was stirred for 10 minutes at -10° C. to obtain a solution of propyl sulfenyl chloride. The solution was cooled to -30° C. and a solution of 22 g of N-methyl-N'-(3,4-dichlorophenyl)-urea in 140 ml of pyridine was added thereto. The mixture was stirred for 5 hours at -20° C., then for 17 hours at 0° C. The mixture was poured into a water-ice-hydrochloric acid-methylene chloride mixture, was stirred and decanted. The organic phase was washed with water, dried and concentrated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with a 9-1 benzene-ethyl acetate mixture. The product was added to petroleum ether (b.p. = 65°-75° C.) and the precipitate formed was recovered by vacuum filtration and was washed and dried to obtain 14 g of N-methyl-N-propylthio-N'-(3,4-dichlorophenyl)-urea melting at 40° C. Analysis: C11 H14 Cl2 N2 OS; molecular weight = 293.22; Calculated: %C, 45.06; %H, 4.81; %Cl, 24.18; %N, 9.55; %S, 10.93; Found: %C, 45.4; %H, 5.0; %Cl, 23.9; %N, 9.8; %S, 11.2.
  • 17
  • N-chloromercaptomorpholine [ No CAS ]
  • [ 3567-62-2 ]
  • [ 41881-53-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran 4.B STEP B STEP B N-methyl-N-morpholinothio-N'-(3,4-dichlorophenyl) urea 43.8 g of N-methyl-N'-(3,4-dichlorophenyl)-urea and 21.1 g of triethylamine were added to 440 ml of tetrahydrofuran and the mixture was stirred until dissolution occurred. A solution of 36 g of N-chloro-mercaptomorpholine in 60 ml of tetrahydrofuran was added in 5 minutes to the said solution and the mixture was stirred for 4 hours at room temperature. The precipitate formed was removed by filtration and the filtrate was concentrated to dryness under reduced pressure. The residue was crystallized from ethyl acetate to obtain 42.5 g of N-methyl-N-morpholinothio-N'-(3,4-dichlorophenyl)-urea melting at 142° C. Analysis: C12 H15 Cl2 N3 O2 S; molecular weight = 336.246; Calculated: %C, 42.86; %H, 4.50; %Cl, 21.09; %N, 12.50; %S, 9.54; Found: %C, 42.8; %H, 4.8; %Cl, 21.0; %N, 12.4; %S, 9.6.
  • 18
  • [ 110-81-6 ]
  • [ 3567-62-2 ]
  • [ 41881-55-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuryl dichloride In pyridine; dichloromethane 6 N-METHYL-N-ETHYLTHIO-N'-(3,4-DICHLOROPHENYL)-UREA EXAMPLE 6 N-METHYL-N-ETHYLTHIO-N'-(3,4-DICHLOROPHENYL)-UREA A solution of 67 g of sulfuryl chloride in 100 ml of methylene chloride was added dropwise to a solution of 61 g of diethyldisulfide in 600 ml of methylene chloride cooled to -40° C. and after the temperature was raised to -5° C., the mixture was stirred for 5 minutes. The mixture was cooled to -40° C. and a solution of 57 g of N-methyl-N'-(3,4-dichlorophenyl)-urea in 460 ml of pyridine was added dropwise thereto. The mixture was stirred at -40° C. for 1 hour and for another hour at -20° C. The mixture was poured into an ice-water mixture and the pH was adjusted to 3.5 by addition of concentrated hydrochloric acid. The organic phase was decanted and the aqueous phase was extracted with methylene chloride. The combined organic phases were washed with water, dried and evaporated to dryness under reduced pressure. The residue was crystallized from isopropyl ether and subjected to chromatography over silica gel. Elution with a 7-3 benzene-ethyl acetate mixture gave 22 g of N-methyl-N-ethylthio-N'-(3,4-dichlorophenyl)-urea melting at 71° C. Analysis: C10 H12 Cl2 N2 OS; molecular weight = 279.16; Calculated: %C, 43.02; %H, 4.34; %Cl, 25.41; %N, 10.04; %S, 11.48; Found: %C, 43.2; %H, 4.4; %Cl, 25.2; %N, 10.1; %S, 11.1.
  • 19
  • [ 420-12-2 ]
  • [ 3567-62-2 ]
  • [ 62351-01-3 ]
YieldReaction ConditionsOperation in experiment
With chlorosulphuric acid In pyridine; dichloromethane 2 N-(2-chloroethylthio)-N-methyl-N'-(3,4-dichlorophenyl)-urea EXAMPLE 2 N-(2-chloroethylthio)-N-methyl-N'-(3,4-dichlorophenyl)-urea 27 g of chlorosulfuric acid were slowly added at 0° C to a mixture of 12 g of ethylene sulfide and 200 ml of methylene chloride and the mixture was stirred at 0° C for 10 minutes and was then cooled to -20° C. A mixture of 32.6 g of N-methyl-N'-(3,4-dichlorophenyl)-urea in 210 ml of pyridine was added to the reaction mixture after which the temperature returned to 0° C. The mixture was stirred at 0° C for 10 minutes and was then poured into a mixture of ice, water, hydrochloric acid and methylene chloride. The mixture was stirred for 30 minutes and the decanted organic phase was washed, dried, filtered and concentrated to dryness under reduced pressure. The residue was chromatographed over silica gel and the product was eluted witn 9-1 benzene-ethyl acetate mixture and was crystallized from isopropyl ether to obtain 10 g of N-(2-chloroethylthio)-N-methyl-N'-(3,4-dichlorophenyl)-urea melting at 62° C. Analysis: C10 H11 Cl3 N2 OS Calculated: %C 38.29; %H 3.54; %N 8.93; %Cl 33.92; %S 10.22; Found: %C 38.3; %H 3.6; %N 8.7; %Cl 33.8; %S 10.0
  • 20
  • [ 14925-97-4 ]
  • [ 629-45-8 ]
  • [ 3567-62-2 ]
  • [ 41881-68-9 ]
YieldReaction ConditionsOperation in experiment
With sulfuryl dichloride In pyridine; dichloromethane 19 N-METHYL-N-n-BUTYLTHIO-N'-(3,4-DICHLOROPHENYL)-UREA EXAMPLE 19 N-METHYL-N-n-BUTYLTHIO-N'-(3,4-DICHLOROPHENYL)-UREA 26.8 g of sulfuryl chloride were slowly added at -30° C. to 35.6 g of dibutyl disulfide and 212 ml of methylene chloride and after raising the temperature to -10° C., the mixture was stirred for 10 minutes at -10° C. to obtain a solution of n-butyl sulfenyl chloride. A solution of 44 g of N-methyl-N'-(3,4-dichlorophenyl)-urea in 280 ml of pyridine was added slowly to the said solution at -30° C. and the mixture was stirred at -20° C. for 5 hours, then at 0° C. for 17 hours and poured into a methylene chloride-water-ice-hydrochloric acid mixture. The mixture was stirred and decanted and the organic phase was washed with water, dried and concentrated to dryness under reduced pressure. The residue was crystallized from methanol to obtain 22.1 g of N-methyl-N-n-butylthio-N'-(3,4-dichlorophenyl)-urea melting at 47° C. Analysis: C12 H16 Cl2 N2 OS; molecular weight = 307.25; Calculated: %C, 46.91; %H, 5.25; %Cl, 23.08; %N, 9.12; %S, 10.44; Found: %C, 47.1; %H, 5.5; %Cl, 23.0 %N, 8.7; %S, 10.7.
  • 21
  • [ 3567-62-2 ]
  • [ 144386-19-6 ]
  • [ 41881-56-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In water; dimethyl sulfoxide 7 N-METHYL-N-(2-THIAPROPYL)-N'-(3,4-DICHLOROPHENYL)-UREA EXAMPLE 7 N-METHYL-N-(2-THIAPROPYL)-N'-(3,4-DICHLOROPHENYL)-UREA 11 g of N-methyl-N'-(3,4-dichlorophenyl)-urea, 60 g of potassium carbonate and 50 ml of dimethylsulfur chloride were added at 10° C. to 150 ml of dimethylsulfoxide and the mixture was allowed to stand until exothermic generation of heat ceased. The reaction mixture was added to water and was extracted with ether. The ether solution was washed with water, dried and concentrated to dryness by distillation under reduced pressure. The residue was crystallized from isopropyl ether and then ethyl acetate to obtain 7.7 g of N-methyl-N-(2-thiapropyl)-N'-(3,4-dichlorophenyl)-urea melting at 103° C.
  • 22
  • [ 3567-62-2 ]
  • [ 1380583-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 0 °C 2: copper(l) chloride / benzene / Reflux
  • 23
  • [ 3567-62-2 ]
  • [ 1380583-56-1 ]
YieldReaction ConditionsOperation in experiment
With carbon tetrabromide; triethylamine; triphenylphosphine In dichloromethane at 0℃;
  • 24
  • [ 3567-62-2 ]
  • N-methyl-N-(2-chlorocycloheptylthio)-N'-(3,4-dichlorophenyl)-urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; sulphur dichloride / dichloromethane
Same Skeleton Products
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