CH632242A5 - Process for preparing 2-acylamino-5-chlorobenzenesulphonic acids - Google Patents

Process for preparing 2-acylamino-5-chlorobenzenesulphonic acids Download PDF

Info

Publication number: CH632242A5
Authority: CH; Switzerland
Prior art keywords: formula; oxidation; acid; carboxy; compounds
Prior art date: 1976-09-03

Application number

CH1062377A

Other languages

German (de)

English (en)

Inventor

Otto Dr Fuchs

Bernhard Dr Mees

Ruediger Dr Berthold

Siegfried Dr Lange

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1976-09-03

Filing date

1977-08-31

Publication date

1982-09-30

1977-08-31 Application filed by Hoechst Ag filed Critical Hoechst Ag

1982-09-30 Publication of CH632242A5 publication Critical patent/CH632242A5/de

Links

239000002253 acid Substances 0.000 title description 5
150000007513 acids Chemical class 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title 1
238000007254 oxidation reaction Methods 0.000 claims description 10
230000003647 oxidation Effects 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 5
239000012736 aqueous medium Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
-1 Isopropyl compound Chemical class 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
239000000049 pigment Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VYZCFAPUHSSYCC-UHFFFAOYSA-N 2-amino-5-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1Cl VYZCFAPUHSSYCC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000004575 stone Substances 0.000 description 2
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
UYEKNNXCZHSNCX-UHFFFAOYSA-N (5-amino-2-chlorophenyl)methanesulfonic acid Chemical compound NC1=CC=C(Cl)C(CS(O)(=O)=O)=C1 UYEKNNXCZHSNCX-UHFFFAOYSA-N 0.000 description 1
VBNFOVAJFHWUAN-UHFFFAOYSA-N 2-acetamido-4-(2-chloroethyl)benzenesulfonic acid Chemical compound ClCCC1=CC=C(C(=C1)NC(C)=O)S(=O)(=O)O VBNFOVAJFHWUAN-UHFFFAOYSA-N 0.000 description 1
VIYONYBARUSSCC-UHFFFAOYSA-N 2-amino-4-(2-chloroethyl)benzenesulfonic acid Chemical compound NC1=CC(CCCl)=CC=C1S(O)(=O)=O VIYONYBARUSSCC-UHFFFAOYSA-N 0.000 description 1
VEPOZWJTGLVFEU-UHFFFAOYSA-N 5-acetamido-2-chloro-4-sulfobenzoic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=C(Cl)C=C1S(O)(=O)=O VEPOZWJTGLVFEU-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
230000019635 sulfation Effects 0.000 description 1
238000005670 sulfation reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1062377A 1976-09-03 1977-08-31 Process for preparing 2-acylamino-5-chlorobenzenesulphonic acids CH632242A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19762639668 DE2639668A1 (de)	1976-09-03	1976-09-03	2-acylamino-5-chlor-benzolsulfonsaeuren

Publications (1)

Publication Number	Publication Date
CH632242A5 true CH632242A5 (en)	1982-09-30

Family

ID=5987047

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1062377A CH632242A5 (en)	1976-09-03	1977-08-31	Process for preparing 2-acylamino-5-chlorobenzenesulphonic acids

Country Status (6)

Country	Link
JP (1)	JPS5331644A (it)
CH (1)	CH632242A5 (it)
DE (1)	DE2639668A1 (it)
FR (1)	FR2363548A1 (it)
GB (1)	GB1584823A (it)
IT (1)	IT1085035B (it)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1436059A (en) *	1974-04-18	1976-05-19	Ici Ltd	2-amino-4,5-disulphobenzoic acid and derivatives

1976
- 1976-09-03 DE DE19762639668 patent/DE2639668A1/de not_active Withdrawn
1977
- 1977-08-31 CH CH1062377A patent/CH632242A5/de not_active IP Right Cessation
- 1977-09-01 IT IT2719177A patent/IT1085035B/it active
- 1977-09-02 JP JP10504977A patent/JPS5331644A/ja active Pending
- 1977-09-02 GB GB3674377A patent/GB1584823A/en not_active Expired
- 1977-09-05 FR FR7726813A patent/FR2363548A1/fr active Granted

Also Published As

Publication number	Publication date
FR2363548A1 (fr)	1978-03-31
FR2363548B1 (it)	1981-06-12
JPS5331644A (en)	1978-03-25
GB1584823A (en)	1981-02-18
DE2639668A1 (de)	1978-03-09
IT1085035B (it)	1985-05-28

Legal Events

Date	Code	Title	Description
1986-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

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