CS261659B1 - Method of steel strips and sheets for enamel production - Google Patents
Method of steel strips and sheets for enamel production Download PDFInfo
- Publication number
- CS261659B1 CS261659B1 CS874448A CS444887A CS261659B1 CS 261659 B1 CS261659 B1 CS 261659B1 CS 874448 A CS874448 A CS 874448A CS 444887 A CS444887 A CS 444887A CS 261659 B1 CS261659 B1 CS 261659B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxo
- pyridazin
- sheets
- chlorophenyl
- steel strips
- Prior art date
Links
- 229910000831 Steel Inorganic materials 0.000 title 1
- 210000003298 dental enamel Anatomy 0.000 title 1
- 239000010959 steel Substances 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- -1 3-trifluoromethyl-4-chlorophenyl Chemical group 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Chemical group 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Chemical group 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- PYAGIKMJHGXHLC-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-methoxy-5-sulfanylpyridazin-3-one Chemical compound O=C1C(OC)=C(S)C=NN1C1=CC=CC(Cl)=C1 PYAGIKMJHGXHLC-UHFFFAOYSA-N 0.000 description 1
- XUTUHLSYOTVJQU-UHFFFAOYSA-N 2-phenyl-4-propan-2-yloxy-5-sulfanylpyridazin-3-one Chemical compound O=C1C(OC(C)C)=C(S)C=NN1C1=CC=CC=C1 XUTUHLSYOTVJQU-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
1,5 g 2-(3-chlórfenyl)-4-metoxy-3-oxo-2H-pyridazín-5-tiolu sa miešalo v 15 ml dimetylformamidu pri refluxe po dobu 4 hodin. Diinetylformamid sa oddestiloval za zničeného tlaku. Zvyšok sa potom prekryštalizoval z etylalkoholu (25 ml). Získalo sa 0,5 g bielej krystalické) látky s t. t. 239—241 °C. Analýza pre CnH9ClN2O2S (m. h. 304,15) vypočítané:1.5 g of 2- (3-chlorophenyl) -4-methoxy-3-oxo-2H-pyridazine-5-thiol were stirred in 15 ml of dimethylformamide at reflux for 4 hours. Diinetylformamide was distilled off under reduced pressure. The residue was then recrystallized from ethanol (25 ml). 0.5 g of a white crystalline substance was obtained with mp 239-241 ° C. Analysis for C 11 H 9 ClN 2 O 2 S (mh 304.15) calculated:
11,66 % Cl, 10,54 % S, zistené:11.66% Cl, 10.54% S, found:
11,86 % Cl, 10,87 % S,11.86% Cl, 10.87% S,
IC v CHCI·,:IC in CHCI · ,:
v (C=O) = 1630 cm'1, v (O—H) — 3 350 cm -'.v (C = O) = 1630 cm -1 , v (O-H) -3 350 cm -1.
Příklad 4Example 4
Příprava 2-fenyl-5-izopropylLio-3-cxo-2H-pyridazín-4-olu g 2-fenyl-4-lzopropyloxy-3-oxo-2H-pyridazín-5-tiolu sa miešal v 15 ml dimetylformamidu pri teplote varu. Dimetylformamid sa oddestiloval za zničeného tlaku. Zvyšok sa prekryštalizoval z etylalkoholu (15 ml). Získalo sa 0,6 g hiele) kryštalickej látky s t. t. 148—149 °C.Preparation of 2-phenyl-5-isopropyl-10-oxo-2H-pyridazin-4-ol 2-phenyl-4-isopropyloxy-3-oxo-2H-pyridazine-5-thiol was stirred in 15 ml of dimethylformamide at boiling point. Dimethylformamide was distilled off under reduced pressure. The residue was recrystallized from ethanol (15 ml). 0.6 g of a crystalline substance with m.p. t. 148-149 ° C.
Analýza pre C/3H/4N2O2S (m. h. = 262,31) vypočítané:Analysis calculated for C / 3 H / 4 N 2 O 2 S (mh = 262.31):
10,68 % N, 12,22 % S, zistené:N, 10.68. Found:
10,89 % N, 12,46 % S.N, 10.89. S, 12.46.
IC v CHC13:IC in CHC1 3 :
v (O=O) = 1 635 cm-1, v (O—H) = 3 320 cm'1.v (0 = O) = 1635 cm -1 , v (0-H) = 3,320 cm -1 .
Příklad 5Example 5
Příprava 2-metyl-5-etyltio-3-oxo-2H-pyridazín-4-olu g sodnej soli 4-etoxy-2-metyl-3-oxo-2H-pyridazín-5-tiolu sa miešalo v 15 ml dimetylformamidu 4 hodiny pri teplote varu. Dimetylformamid sa oddestiloval za zničeného tlaku. Zvyšok sa rozpustil vo vodě a přidala sa 37 %-ná kyselina chlorovodíková do pH = 1. Vylúčená tuhá látka sa odfiltrovala, prekryštalizovala z metylalkoholu. Získalo sa 0,5 g bielej kryštalickej látky s t. t. 152—151 °C.Preparation of 2-methyl-5-ethylthio-3-oxo-2H-pyridazin-4-ol 4-ethoxy-2-methyl-3-oxo-2H-pyridazine-5-thiol sodium salt was stirred in 15 ml of dimethylformamide for 4 hours at boiling point. Dimethylformamide was distilled off under reduced pressure. The residue was dissolved in water and 37% hydrochloric acid was added until pH = 1. The precipitated solid was filtered off, recrystallized from methanol. 0.5 g of a white crystalline substance with m.p. t. Mp 152-151 ° C.
Analýza pre C7H10N2O2S (m. h. — 186,22) vypočítané:Analysis for C 7 H 10 N 2 O 2 S (mh - 186.22) calculated:
15,03 % N, 17,22 % S, zistené:15.03% N, 17.22% S, found:
15,22 % N, 17,50 % S.N, 15.22; S, 17.50.
IC v CHClp v (C=O) = 1 618 cm'1, v (O—H) = 3 368 cm-1.IC in CHCl3 v (C = O) = 1618 cm -1 , v (O-H) = 3,368 cm -1 .
Příklad 6Example 6
Příprava 2- (3-tolyl j-5-metyltio-3-oxo-2H-pyridazín-4-olu g sodnej soli 4-metoxy-2-( 3-tolyl )-3-oxo-2H-pyridazín-5-tiolu sa miešala v 40 ml etylalkoholu pri refluxe 4 hodiny. Etylalkohol sa oddestiloval za zničeného tlaku. Zvyšok sa rozpustil vo vede a přidala sa 37 °/o-ná kyselina chlorovodíková do pl-í = 1. Vylúčená tuhá látka sa odfiltrovala a prekryštalizovala z etylalkoholu. Získalo sa 1,3 g bielej kryštalickej látky s t. t. 2253—230 °C. Analýza pre Cj2H12N2O2S (m. h. = 248,88) vypočítané:Preparation of 2- (3-tolyl) -5-methylthio-3-oxo-2H-pyridazin-4-ol 4-methoxy-2- (3-tolyl) -3-oxo-2H-pyridazine-5-thiol sodium salt The mixture was stirred in 40 ml of ethyl alcohol at reflux for 4 hours, the ethyl alcohol was distilled off under reduced pressure, the residue was dissolved in science and 37% hydrochloric acid was added to pH = 1. The precipitated solid was filtered and recrystallized from ethyl alcohol. . 1.3 g of a white crystalline solid, mp 2253-230 ° C. analysis for C 2 H 12 N 2 O 2 s (MW = 248.88) calculated:
11,28 % N, 12,91 % S, zistené:N 11.28%, S 12.91%, found:
11,39 % N, 13,11 % S.N, 11.39. S, 13.11.
IČ v CHC13:IR in CHC1 3 :
v (C=O) = 1 620 cm“1, v (O—Hj == 3 360 cm-1.v (C = O) = 1620 cm -1 , v (H = H = 3560 cm -1 ) .
Podobným postupom bolí připravené:In a similar way, it hurts:
2-cyklohexyl-5-etyltio-3-oxo-2H-pyridazín-4-ol, t. t. == 150—151 °C, 2-benzyl-5-metyltio-3-oxo-2H-pyridazín-4-ol,2-cyclohexyl-5-ethylthio-3-oxo-2H-pyridazin-4-ol; t. = 150-151 ° C, 2-benzyl-5-methylthio-3-oxo-2H-pyridazin-4-ol,
t. t. = 180—182 °C,t. t. = 180-182 ° C,
2-butyl-5-trietyltio-3-oxo-2H-pyridazín-4-ol, t .t. = 121—123 qC,2-butyl-5-triethylthio-3-oxo-2H-pyridazin-4-ol, m.p. = 121—123 q C,
2- (3-trif luormetyl-4-chlorf enyl) -5-metyltio-3-oxo-2H-pyridazín-4-ol, t. t. — 261—263 stupňov Celzia.2- (3-Trifluoromethyl-4-chlorophenyl) -5-methylthio-3-oxo-2H-pyridazin-4-ol, m.p. t. - 261—263 degrees Celsius.
Příklad 7Example 7
Příprava 2 motyl-5-metyltio-3-oxo-2H-pyridazín-4-olu g sodnej soli 2-nietyl-4-metoxy-3-oxo-2H-pyridazínu sa miešalo v 50 ml vody pri refluxe 4 hodiny. Po ochladnutí reakčnej zmesi na 5 °C sa upravilo pH na 1. Vylúčená tuhá látka sa odfiltrovala, vysušila a prekryštalizovala z toluénu (50 ml). Získalo sa 1,8 gramov kryštalickej látky s t. t.: 156—158 stupňov Celzia, identickej s príkladom 1.Preparation of 2-methyl-5-methylthio-3-oxo-2H-pyridazin-4-ol 2-methyl-4-methoxy-3-oxo-2H-pyridazine sodium salt was stirred in 50 ml of water at reflux for 4 hours. After cooling the reaction mixture to 5 ° C, the pH was adjusted to 1. The precipitated solid was filtered off, dried and recrystallized from toluene (50 ml). 1.8 g of crystalline substance with m.p. t: 156-158 degrees Celsius, identical to Example 1.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS874448A CS261659B1 (en) | 1987-06-17 | 1987-06-17 | Method of steel strips and sheets for enamel production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS874448A CS261659B1 (en) | 1987-06-17 | 1987-06-17 | Method of steel strips and sheets for enamel production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS444887A1 CS444887A1 (en) | 1988-07-15 |
| CS261659B1 true CS261659B1 (en) | 1989-02-10 |
Family
ID=5387234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS874448A CS261659B1 (en) | 1987-06-17 | 1987-06-17 | Method of steel strips and sheets for enamel production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS261659B1 (en) |
-
1987
- 1987-06-17 CS CS874448A patent/CS261659B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS444887A1 (en) | 1988-07-15 |
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