DE192075C - - Google Patents
Info
- Publication number
- DE192075C DE192075C DE1905192075D DE192075DA DE192075C DE 192075 C DE192075 C DE 192075C DE 1905192075 D DE1905192075 D DE 1905192075D DE 192075D A DE192075D A DE 192075DA DE 192075 C DE192075 C DE 192075C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carboxylic acid
- oxy
- water
- thioglycol
- 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 - Lifetime
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 229940106681 chloroacetic acid Drugs 0.000 claims description 6
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229940103494 thiosalicylic acid Drugs 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- XHQBIYCRFVVHFD-UHFFFAOYSA-N 1-benzothiophen-3-ol Chemical group C1=CC=C2C(O)=CSC2=C1 XHQBIYCRFVVHFD-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- -1 chloroacetic acid ester Chemical class 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims 2
- OLBAMNTVQSDZQI-UHFFFAOYSA-N 2-(sulfoamino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1NS(O)(=O)=O OLBAMNTVQSDZQI-UHFFFAOYSA-N 0.000 claims 1
- MOTOSAGBNXXRRE-UHFFFAOYSA-N 2-phenylsulfanylacetic acid Chemical compound OC(=O)CSC1=CC=CC=C1 MOTOSAGBNXXRRE-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000012230 colorless oil Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical compound C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/64—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT34780D AT34780B (de) | 1905-05-08 | 1907-07-04 | Verfahren zur Darstellung der 3-Oxy(1)thionaphten-2-karbonsäure (Thioindoxylkarbonsäure) oder von Gemischen dieser Säure mit 3-Oxy(1)thionaphten (Thioindoxyl). |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE198712T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE192075C true DE192075C (enrdf_load_stackoverflow) |
Family
ID=33035719
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT198713D Active DE198713C (enrdf_load_stackoverflow) | |||
| DE1905192075D Expired - Lifetime DE192075C (enrdf_load_stackoverflow) | 1905-05-08 | 1905-05-08 | |
| DE1905198712D Expired - Lifetime DE198712C (enrdf_load_stackoverflow) | 1905-08-09 | 1905-08-09 | |
| DE1905196016D Expired - Lifetime DE196016C (enrdf_load_stackoverflow) | 1905-10-18 | 1905-10-18 | |
| DE1906232277D Expired - Lifetime DE232277C (enrdf_load_stackoverflow) | 1906-11-29 | 1906-11-29 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT198713D Active DE198713C (enrdf_load_stackoverflow) |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1905198712D Expired - Lifetime DE198712C (enrdf_load_stackoverflow) | 1905-08-09 | 1905-08-09 | |
| DE1905196016D Expired - Lifetime DE196016C (enrdf_load_stackoverflow) | 1905-10-18 | 1905-10-18 | |
| DE1906232277D Expired - Lifetime DE232277C (enrdf_load_stackoverflow) | 1906-11-29 | 1906-11-29 |
Country Status (1)
| Country | Link |
|---|---|
| DE (5) | DE192075C (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040016046A1 (en) * | 2002-07-26 | 2004-01-29 | Siegal David M. | Push-on bolt stabilizer |
-
0
- DE DENDAT198713D patent/DE198713C/de active Active
-
1905
- 1905-05-08 DE DE1905192075D patent/DE192075C/de not_active Expired - Lifetime
- 1905-08-09 DE DE1905198712D patent/DE198712C/de not_active Expired - Lifetime
- 1905-10-18 DE DE1905196016D patent/DE196016C/de not_active Expired - Lifetime
-
1906
- 1906-11-29 DE DE1906232277D patent/DE232277C/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE198712C (enrdf_load_stackoverflow) | |
| DE198713C (enrdf_load_stackoverflow) | |
| DE232277C (enrdf_load_stackoverflow) | |
| DE196016C (enrdf_load_stackoverflow) |
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