GB731020A - Process for the manufacture of 4-(p-aminobenzenesulphonyl)-aminopyrimidines - Google Patents
Process for the manufacture of 4-(p-aminobenzenesulphonyl)-aminopyrimidinesInfo
- Publication number
- GB731020A GB731020A GB14396/53A GB1439653A GB731020A GB 731020 A GB731020 A GB 731020A GB 14396/53 A GB14396/53 A GB 14396/53A GB 1439653 A GB1439653 A GB 1439653A GB 731020 A GB731020 A GB 731020A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimethylamine
- hydrolysis
- followed
- amino
- reduction
- 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
- BWCQFACLGZISKP-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonylpyrimidin-2-amine Chemical class NC1=CC=C(C=C1)S(=O)(=O)C1=NC(=NC=C1)N BWCQFACLGZISKP-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- 230000007062 hydrolysis Effects 0.000 abstract 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- BJJDXAFKCKSLTE-UHFFFAOYSA-N 2,6-dimethylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(C)=N1 BJJDXAFKCKSLTE-UHFFFAOYSA-N 0.000 abstract 1
- VNQBDDXIHRUBIO-UHFFFAOYSA-N 4,6-bis(benzenesulfonyl)pyrimidin-2-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=CC(=NC(=N1)N)S(=O)(=O)C1=CC=CC=C1 VNQBDDXIHRUBIO-UHFFFAOYSA-N 0.000 abstract 1
- FVNKPYJXKFDZOT-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonyl-2,6-dimethylpyrimidin-5-amine Chemical compound NC1=CC=C(C=C1)S(=O)(=O)C1=NC(=NC(=C1N)C)C FVNKPYJXKFDZOT-UHFFFAOYSA-N 0.000 abstract 1
- YFLKVSOKVKZERQ-UHFFFAOYSA-N 4-acetyl-4-aminocyclohexa-1,5-diene-1-sulfonyl chloride Chemical compound CC(=O)C1(N)CC=C(S(Cl)(=O)=O)C=C1 YFLKVSOKVKZERQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 abstract 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- -1 sulpho group Chemical group 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE316968X | 1952-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB731020A true GB731020A (en) | 1955-06-01 |
Family
ID=6150634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14396/53A Expired GB731020A (en) | 1952-05-26 | 1953-05-21 | Process for the manufacture of 4-(p-aminobenzenesulphonyl)-aminopyrimidines |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE520222A (enrdf_load_stackoverflow) |
| CH (1) | CH316968A (enrdf_load_stackoverflow) |
| FR (1) | FR1089956A (enrdf_load_stackoverflow) |
| GB (1) | GB731020A (enrdf_load_stackoverflow) |
| NL (1) | NL82164C (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2792391A (en) * | 1954-06-15 | 1957-05-14 | Ciba Pharm Prod Inc | Process for the manufacture of sulfonamides |
-
0
- NL NL82164D patent/NL82164C/xx active
- BE BE520222D patent/BE520222A/xx unknown
-
1953
- 1953-04-10 CH CH316968D patent/CH316968A/de unknown
- 1953-05-18 FR FR1089956D patent/FR1089956A/fr not_active Expired
- 1953-05-21 GB GB14396/53A patent/GB731020A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1089956A (fr) | 1955-03-25 |
| NL82164C (enrdf_load_stackoverflow) | |
| CH316968A (de) | 1956-10-31 |
| BE520222A (enrdf_load_stackoverflow) |
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