DE1932690A1 - Verfahren zur Herstellung neuer substituierter Isothiocyanate - Google Patents
Verfahren zur Herstellung neuer substituierter IsothiocyanateInfo
- Publication number
- DE1932690A1 DE1932690A1 DE19691932690 DE1932690A DE1932690A1 DE 1932690 A1 DE1932690 A1 DE 1932690A1 DE 19691932690 DE19691932690 DE 19691932690 DE 1932690 A DE1932690 A DE 1932690A DE 1932690 A1 DE1932690 A1 DE 1932690A1
- Authority
- DE
- Germany
- Prior art keywords
- chloroform
- water
- isothiocyanates
- yield
- solvent
- 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.)
- Pending
Links
- 150000002540 isothiocyanates Chemical class 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 91
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 18
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 10
- -1 alkaline earth metal carbonates Chemical class 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 5
- 230000000078 anti-malarial effect Effects 0.000 claims description 4
- 230000000845 anti-microbial effect Effects 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 230000001549 tubercolostatic effect Effects 0.000 claims description 4
- 239000000814 tuberculostatic agent Substances 0.000 claims description 4
- 239000003430 antimalarial agent Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 230000005484 gravity Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000003208 petroleum Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- DOSQODOJAWJBQB-UHFFFAOYSA-N (4-aminophenyl)-(4-bromophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(Br)C=C1 DOSQODOJAWJBQB-UHFFFAOYSA-N 0.000 description 1
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
- FMSYGGOEIOBUOR-UHFFFAOYSA-N (4-isothiocyanatophenyl)-phenylmethanone Chemical compound C=1C=C(N=C=S)C=CC=1C(=O)C1=CC=CC=C1 FMSYGGOEIOBUOR-UHFFFAOYSA-N 0.000 description 1
- ODCATTUUPYWMMI-DHZHZOJOSA-N (e)-3-(4-aminophenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC(N)=CC=C1\C=C\C(=O)C1=CC=CC=C1 ODCATTUUPYWMMI-DHZHZOJOSA-N 0.000 description 1
- BJWWWAZDCHGYTO-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one Chemical compound C1=CC(N(C)C)=CC=C1C=CC(=O)C1=CC=C(N)C=C1 BJWWWAZDCHGYTO-UHFFFAOYSA-N 0.000 description 1
- MPNVWXWBSJKVDD-UHFFFAOYSA-N 1-isothiocyanato-4-[(4-isothiocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=S)=CC=C1CC1=CC=C(N=C=S)C=C1 MPNVWXWBSJKVDD-UHFFFAOYSA-N 0.000 description 1
- TZCMYPASAIZADP-UHFFFAOYSA-N 3-(4-aminophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)C=CC1=CC=C(N)C=C1 TZCMYPASAIZADP-UHFFFAOYSA-N 0.000 description 1
- PBKCJNOFHGLNEZ-UHFFFAOYSA-N 4-[(4-methylphenyl)diazenyl]aniline Chemical compound C1=CC(C)=CC=C1N=NC1=CC=C(N)C=C1 PBKCJNOFHGLNEZ-UHFFFAOYSA-N 0.000 description 1
- WDTRNCFZFQIWLM-UHFFFAOYSA-N 4-benzylaniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1 WDTRNCFZFQIWLM-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004781 supercooling Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS538068 | 1968-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1932690A1 true DE1932690A1 (de) | 1970-01-29 |
Family
ID=5398586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691932690 Pending DE1932690A1 (de) | 1968-07-23 | 1969-06-27 | Verfahren zur Herstellung neuer substituierter Isothiocyanate |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH514559A (enrdf_load_stackoverflow) |
| DE (1) | DE1932690A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2014688B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1228516A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053915A1 (en) * | 1980-12-04 | 1982-06-16 | Lilly Industries Limited | Novel compounds and hapten-immunoglobulin conjugates derived from them |
| US5229503A (en) * | 1988-05-10 | 1993-07-20 | Ciba-Geigy Corporation | Lysine-n-amino reactive and cysteine-mercapto reactive azo dyes |
| US5382659A (en) * | 1988-05-10 | 1995-01-17 | Ciba-Geigy Corp. | Aromatic acids |
-
1969
- 1969-05-20 CH CH774369A patent/CH514559A/de not_active IP Right Cessation
- 1969-06-13 GB GB1228516D patent/GB1228516A/en not_active Expired
- 1969-06-27 DE DE19691932690 patent/DE1932690A1/de active Pending
- 1969-07-21 FR FR6924716A patent/FR2014688B1/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053915A1 (en) * | 1980-12-04 | 1982-06-16 | Lilly Industries Limited | Novel compounds and hapten-immunoglobulin conjugates derived from them |
| US5229503A (en) * | 1988-05-10 | 1993-07-20 | Ciba-Geigy Corporation | Lysine-n-amino reactive and cysteine-mercapto reactive azo dyes |
| US5382659A (en) * | 1988-05-10 | 1995-01-17 | Ciba-Geigy Corp. | Aromatic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2014688B1 (enrdf_load_stackoverflow) | 1973-06-08 |
| GB1228516A (enrdf_load_stackoverflow) | 1971-04-15 |
| CH514559A (de) | 1971-10-31 |
| FR2014688A1 (enrdf_load_stackoverflow) | 1970-04-17 |
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