GB815274A - Preparation of sulphonyl chlorides of organic cyano compounds - Google Patents
Preparation of sulphonyl chlorides of organic cyano compoundsInfo
- Publication number
- GB815274A GB815274A GB3899956A GB3899956A GB815274A GB 815274 A GB815274 A GB 815274A GB 3899956 A GB3899956 A GB 3899956A GB 3899956 A GB3899956 A GB 3899956A GB 815274 A GB815274 A GB 815274A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- sulphonyl
- cyano
- preparation
- chlorides
- 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.)
- Expired
Links
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 title abstract 7
- 125000004093 cyano group Chemical group *C#N 0.000 title abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 150000001263 acyl chlorides Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 235000011007 phosphoric acid Nutrition 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 229960001663 sulfanilamide Drugs 0.000 abstract 2
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 abstract 1
- DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 abstract 1
- SLOUONJOMMMJGD-UHFFFAOYSA-N 4-cyanocyclohexane-1-sulfonyl chloride Chemical compound ClS(=O)(=O)C1CCC(C#N)CC1 SLOUONJOMMMJGD-UHFFFAOYSA-N 0.000 abstract 1
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 abstract 1
- VNBDOZRYYRXFQQ-UHFFFAOYSA-N 5-cyanofuran-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)O1 VNBDOZRYYRXFQQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910020364 ClSO2 Inorganic materials 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- HFAGGNFWBMENHF-UHFFFAOYSA-N S(=O)(=O)(Cl)Cl.C(#N)C1=CC(=CC=C1)[N+](=O)[O-] Chemical compound S(=O)(=O)(Cl)Cl.C(#N)C1=CC(=CC=C1)[N+](=O)[O-] HFAGGNFWBMENHF-UHFFFAOYSA-N 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 125000005418 aryl aryl group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N benzenesulfonimidic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- -1 sulphamoyl Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In a process for the preparation of cyano organic sulphonyl chlorides ClSO2.A.CN, wherein A is a divalent organic group, the corresponding trichlorophosphazosulphonylacyl chloride Cl3P=N.O2S.A.COCl, is heated at 150-190 DEG C. in the presence of a conversion moderator, which is an aryl or substituted aryl sulphonamide, preferably benzene or toluene sulphonamide, a sulphonyl chloride, preferably a sulphonyl chloride which is a previous preparation of that which is to be produced by the process, an inorganic acid of phosphorus, preferably orthophosphoric acid, or a small amount of water, preferably in the form of moist air. The reaction is desirably carried out under reduced pressure so that liberated phosphoryl chloride distils from the reaction mixture and the amounts of moderator used are 2-10 parts of sulphonamide per 100 parts of acyl chloride, not more than 10 per cent w/w of sulphonyl chloride, 0.01-0.05 mol. of an inorganic acid of phosphorus per mol. of acyl chloride, and 0.1-2 per cent w/w of water. Examples include the preparation of the following sulphonyl chlorides: p-cyanobenzenesulphonyl chloride, 2-cyano - 5 - furansulphonyl chloride, 1 : 8 - di - cyano - 4 : 5 - naphthalene - disulphonyl chloride, p-cyanocyclohexylsulphonyl chloride and 4 - cyano - 2 - nitrobenzene sulphonyl chloride, using as conversion moderators benzene-, b -toluene-, a -naphthalene-, and p-nitrobenzenesulphonamides, 96.6 per cent or 85 per cent phosphoric acid, water or moist air, and the sulphonyl chlorides to be prepared. Trichlorophosphazosulphonylacyl chlorides are prepared by reacting a sulphamoyl organic carboxylic acid with phosphorus pentachloride in the presence of phosphorus oxychloride.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB815274A true GB815274A (en) | 1959-06-24 |
Family
ID=1745433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3899956A Expired GB815274A (en) | 1956-12-21 | Preparation of sulphonyl chlorides of organic cyano compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB815274A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026304A (en) * | 1959-12-18 | 1962-03-20 | Du Pont | Halothioformylcyanides and homopolymers thereof |
-
1956
- 1956-12-21 GB GB3899956A patent/GB815274A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026304A (en) * | 1959-12-18 | 1962-03-20 | Du Pont | Halothioformylcyanides and homopolymers thereof |
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