DE2230070A1 - Verfahren zur Herstellung von N-(2,4-Dihalogen-s-triazin-6-yl)-harnstoffen - Google Patents
Verfahren zur Herstellung von N-(2,4-Dihalogen-s-triazin-6-yl)-harnstoffenInfo
- Publication number
- DE2230070A1 DE2230070A1 DE19722230070 DE2230070A DE2230070A1 DE 2230070 A1 DE2230070 A1 DE 2230070A1 DE 19722230070 DE19722230070 DE 19722230070 DE 2230070 A DE2230070 A DE 2230070A DE 2230070 A1 DE2230070 A1 DE 2230070A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- preparation
- reaction
- triazin
- primary
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- 235000013877 carbamide Nutrition 0.000 title description 2
- 150000003672 ureas Chemical class 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- -1 heterocyclic amines Chemical class 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OUNAMPCGUYODKG-UHFFFAOYSA-N (4,6-dichloro-1,3,5-triazin-2-yl)urea Chemical compound NC(=O)NC1=NC(Cl)=NC(Cl)=N1 OUNAMPCGUYODKG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- GRVHWSMDYSGRMD-UHFFFAOYSA-N 2-isocyanato-1,3,5-triazine Chemical class O=C=NC1=NC=NC=N1 GRVHWSMDYSGRMD-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH910271 | 1971-06-22 | ||
| CH610072A CH562229A5 (en) | 1972-04-25 | 1972-04-25 | Dihalo-triazinyl-ureas - from is cyanates and ammonia or amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2230070A1 true DE2230070A1 (de) | 1972-12-28 |
Family
ID=25698975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722230070 Ceased DE2230070A1 (de) | 1971-06-22 | 1972-06-20 | Verfahren zur Herstellung von N-(2,4-Dihalogen-s-triazin-6-yl)-harnstoffen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3849413A (enExample) |
| JP (1) | JPS5649911B1 (enExample) |
| AR (1) | AR194249A1 (enExample) |
| BE (1) | BE785174A (enExample) |
| DE (1) | DE2230070A1 (enExample) |
| FR (1) | FR2143021B1 (enExample) |
| IT (1) | IT958450B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2500427A1 (de) | 1974-01-09 | 1975-07-17 | Ciba Geigy Ag | Bis-dihalogen-s-triazinyl-harnstoffe |
| WO2005030735A1 (en) * | 2003-09-25 | 2005-04-07 | Ranbaxy Laboratories Limited | Triazines derivatives as cell adhesion inhibitors |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH580607A5 (enExample) * | 1973-08-17 | 1976-10-15 | Ciba Geigy Ag | |
| DE2350414C3 (de) * | 1973-10-08 | 1980-01-10 | Hoechst Ag, 6000 Frankfurt | Substituierte Hydroxyphenyl-ureidos-tri azine |
| CN103497165B (zh) * | 2013-10-09 | 2016-03-09 | 江南大学 | 一种纤维素改性剂的合成方法 |
-
1972
- 1972-06-08 US US00260878A patent/US3849413A/en not_active Expired - Lifetime
- 1972-06-15 FR FR727221661A patent/FR2143021B1/fr not_active Expired
- 1972-06-19 JP JP6053272A patent/JPS5649911B1/ja active Pending
- 1972-06-20 DE DE19722230070 patent/DE2230070A1/de not_active Ceased
- 1972-06-20 IT IT51011/72A patent/IT958450B/it active
- 1972-06-21 BE BE785174A patent/BE785174A/xx unknown
- 1972-06-21 AR AR242655A patent/AR194249A1/es active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2500427A1 (de) | 1974-01-09 | 1975-07-17 | Ciba Geigy Ag | Bis-dihalogen-s-triazinyl-harnstoffe |
| WO2005030735A1 (en) * | 2003-09-25 | 2005-04-07 | Ranbaxy Laboratories Limited | Triazines derivatives as cell adhesion inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| US3849413A (en) | 1974-11-19 |
| IT958450B (it) | 1973-10-20 |
| AR194249A1 (es) | 1973-06-29 |
| BE785174A (fr) | 1972-12-21 |
| FR2143021B1 (enExample) | 1973-07-13 |
| JPS5649911B1 (enExample) | 1981-11-25 |
| FR2143021A1 (enExample) | 1973-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |