GB601329A - Improvements in or relating to the manufacture of substituted ªÏ-(benzenesulphonyl)-acetophenones - Google Patents
Improvements in or relating to the manufacture of substituted ªÏ-(benzenesulphonyl)-acetophenonesInfo
- Publication number
- GB601329A GB601329A GB2544245A GB2544245A GB601329A GB 601329 A GB601329 A GB 601329A GB 2544245 A GB2544245 A GB 2544245A GB 2544245 A GB2544245 A GB 2544245A GB 601329 A GB601329 A GB 601329A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- aminobenzenesulphonyl
- sodium salt
- benzenesulphonyl
- acetophenones
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000003277 amino group Chemical group 0.000 abstract 3
- 159000000000 sodium salts Chemical class 0.000 abstract 3
- YDQNDKBOOVXRTL-UHFFFAOYSA-N 4-acetamidobenzenesulfinic acid Chemical compound CC(=O)NC1=CC=C(S(O)=O)C=C1 YDQNDKBOOVXRTL-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000460 chlorine Chemical group 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- LEQXWOPVKMSPDV-UHFFFAOYSA-N 1-(2-chloro-4-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(O)C=C1Cl LEQXWOPVKMSPDV-UHFFFAOYSA-N 0.000 abstract 1
- NFZVSJDHYISNII-UHFFFAOYSA-N 1-[2-(benzenesulfonyl)phenyl]ethanone Chemical class CC(=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 NFZVSJDHYISNII-UHFFFAOYSA-N 0.000 abstract 1
- FLIMNTHPRIENQI-UHFFFAOYSA-N 4-(acetamidomethyl)benzenesulfinic acid Chemical compound CC(=O)NCC1=CC=C(S(O)=O)C=C1 FLIMNTHPRIENQI-UHFFFAOYSA-N 0.000 abstract 1
- XUQMKUAJGHLWEP-UHFFFAOYSA-N N-(4-acetyl-3-chlorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C(C)=O)C(Cl)=C1 XUQMKUAJGHLWEP-UHFFFAOYSA-N 0.000 abstract 1
- ZPRIDRKRBPTGBT-UHFFFAOYSA-N NC1=CC=C(C=C1)S(=O)(=O)C1=C(C=CC(=C1)N)C(C)=O Chemical compound NC1=CC=C(C=C1)S(=O)(=O)C1=C(C=CC(=C1)N)C(C)=O ZPRIDRKRBPTGBT-UHFFFAOYSA-N 0.000 abstract 1
- NUBVTCSLRWAYIB-UHFFFAOYSA-N NC1=CC=C(C=C1)S(=O)(=O)C1=C(C=CC(=C1)O)C(C)=O Chemical compound NC1=CC=C(C=C1)S(=O)(=O)C1=C(C=CC(=C1)O)C(C)=O NUBVTCSLRWAYIB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 230000005591 charge neutralization Effects 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 230000001264 neutralization Effects 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
Abstract
Substituted o - (benzenesulphonyl) - acetophenones of the general formula <FORM:0601329/IV(b)/1> wherein R1 represents hydrogen, chlorine or bromine, R2 a halogen atom or a hydroxy or amino group and R3 an amino or aminomethyl group, are manufactured by condensing an o -halogenoacetophenone <FORM:0601329/IV(b)/2> (wherein R4 represents a halogen atom or a hydroxy or acylamino group and X chlorine, bromine or iodine) with an alkali metal salt of a sulphinic acid. <FORM:0601329/IV(b)/3> (wherein R5 represents an amine or aminomethyl group protected by an acyl residue) in an inert solvent, and hydrolysing the product to the free amino compound with dilute mineral acid. In examples: (1) the sodium salt of p-acetaminobenzenesulphinic acid is refluxed with o - chloro - p - acetaminoacetophenone in ethanol, and the product is boiled with 2N-hydrochloric acid to produce (after neutralization) o - (p - aminobenzenesulphonyl) - p - aminoacetophenone; (2) o : 2 : 4-trichloroacetophenone similarly yields o -(p-aminobenzenesulphonyl) - 2 : 4 - dichloroacetophenone; (3) o - chloro - p - hydroxyacetophenone similarly gives o - (p - aminobenzenesulphonyl)-p-hydroxyacetophenone; (4), (5) and (6) the sodium salt of p-acetaminobenzenesulphinic acid in (1), (2) and (3) respectively is replaced by the sodium salt of p-acetaminomethyl-benzene sulphinic acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB601329A true GB601329A (en) | 1948-05-04 |
Family
ID=1739232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2544245A Expired GB601329A (en) | 1945-10-01 | Improvements in or relating to the manufacture of substituted ªÏ-(benzenesulphonyl)-acetophenones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB601329A (en) |
-
1945
- 1945-10-01 GB GB2544245A patent/GB601329A/en not_active Expired
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