GB782420A - New hydrazides - Google Patents
New hydrazidesInfo
- Publication number
- GB782420A GB782420A GB2443254A GB2443254A GB782420A GB 782420 A GB782420 A GB 782420A GB 2443254 A GB2443254 A GB 2443254A GB 2443254 A GB2443254 A GB 2443254A GB 782420 A GB782420 A GB 782420A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetyl
- hydrazine
- methyl
- nitrophenylthio
- group
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises hydrazides of the formula A-S-(CH2)n-CO-NR1-NR2R3 wherein A is hydrogen, or a hydrocarbon radical which may be substituted by one or more amino, nitro, methyl, chloro, acetylamino or propionylamino radicals, or A is an acyl radical which may contain a nitro group, or A is the group -(CH2)nCO-NR1-NR2R3 or -S-(CH2)n-CO-NR1-NR2R3, wherein R1 and R2 are hydrogen or alkyl, R3 is hydrogen or an alkyl or acetyl radical and n is 1 or 2, excluding thioglycolic hydrazide. The hydrazides may be prepared (a) by reacting NHR1-NR2R3 or a salt or hydrate thereof with an acylating derivative, e.g. a halide, amide, ester or anhydride, of the acid A-S-(CH2)n-COOH, preferably by heating in an inert solvent such as water or an alcohol; (b) when R1, R2 and R3 are all alkyl radicals, by reacting ASH with Hal-(CH2)n-CO-NR1-NR2R3 in presence of an acid-binding agent, or by using an alkali metal derivative of ASH in absence of such an agent; (c) for compounds where A is a substituted or unsubstituted hydrocarbon or acyl radical, by reacting HS-(CH2)n-CO-NR1NR2R3 either with DHal (where D is a substituted or unsubstituted hydrocarbon radical) in presence of an acid-binding agent, e.g. Na2CO3 or NaOH, or with an acylating derivative, e.g. a halide or anhydride or the corresponding thioacid E.COSH, of the acid E.COOH (wherein E is a hydrocarbon group which may be substituted by a nitro group); (d) for compounds where A is an acylamino substituted hydrocarbon group and R3 is alkyl or acetyl, by acylation of the corresponding amino substituted compound; (e) when R3 is an acetyl group, by acetylating A-S-(CH2)n-CO-NR1-NHR2 provided A does not contain an amino group; (f) where A is a hydrocarbon radical containing at least one acetylamino group, R1 and R2 are hydrogen and R3 is acetyl, by acetylating B-S-(CH2)n-CO-NH-NH2 (wherein B is a hydrocarbon radical containing at least one amino group). In examples: (1) to (9) hydrazine or its hydrate and the appropriately substituted ethyl or methyl thioacetate, thiopropionate or thiodiglycollate give 2-(methylthio)-, 2-(ethylthio)-and 2-(allylthio) acethydrazide, the latter as its hydrochloride, b - mercapto - propionhydrazide hydrochloride, monothiodiglycollic dihydrazide, 2 - (p - chlorophenylthio)-, 2 - (p - nitrophenylthio)-, 2 - (o - nitrophenylthio)-, 2 - (21:41 - dinitrophenylthio)-, 2 - (p - methylphenylthio)-, 2 - (o - methylphenylthio)-, 2 - (21 - methyl - 41 - chlorophenylthio)-, 2 - phenylthio-, 2 - (p-aminophenylthio)-, 2 - (p - acetylaminophenylthio)- and 2 - (p - propionylaminophenylthio)-acethydrazide, and 3-(p-nitrophenylthio) propionhydrazide; (10) 2-(p-acetylaminophenylthio) acethydrazide is acetylated to N-[2-(p-acetylaminophenylthio) acetyl]-N1-acetylhydrazine; (11) to (13) N-acetyl-N1-thioglycollylhydrazine with, respectively, p-chloro-nitrobenzene, benzyl halide, p-nitrobenzoyl chloride and thioacetic acid gives N-acetyl-N1-[2-(p-nitrophenylthio) acetyl] hydrazine, N-acetyl-N1 - [2 - (benzylthio) acetyl] hydrazine, N-acetyl-N1 - [2 - (p - nitrobenzoylthio) acetyl] hydrazine and N - acetyl - N1 - 2 - (acetylthio) - acetyl hydrazine; (14) methyl hydrazine sulphate and methyl 2 - (p - nitrophenylthio) acetate give N - methyl - N1 - 2 - (p - nitrophenylthio) acetyl-hydrazine; (15) and (16) 1 : 1-dimethylhydrazine and trimethylhydrazine give, respectively, with 2 - (p - nitrophenylthio) acetyl chloride, 1 : 1 - dimethyl - 2 - [21 - (p - nitrophenylthio) acetyl] hydrazine and N : N : N1-trimethyl-N1-2 - (p - nitrophenylthioacetyl) hydrazine; (17) chloroacetyltrimethylhydrazine and sodium-p-nitrothiophenate give the product of (16); (18) and (19) thioglycollic hydrazide and, separately, 2 - (p - aminophenylthio) acethydrazide are acetylated to give, respectively, N-acetyl-N1-thioglycollyhydrazine and N-[2-(p-acetylaminophenylthio) acetyl] - N1 - acetylhydrazine; the following are similarly prepared:-N-acetyl-N1-2-(phenylthio) acetylhydrazine, N : N1-diacetyl-monothiodiglycollicdihydrazide, N-acetyl-N1-[2 - (p - nitrophenylthio) acetyl] hydrazine, N - acetyl - [2 - (41 - chloro - 21 - methyl - phenylthio) acetyl] hydrazine and N-acetyl-N1-[2-(p-propionylaminophenylthio) acetyl] hydrazine; (20) diethyl dithiodiglycollate and hydrazine hydrate give dithioglycollic dihydrazide. In the Provisional Specification the substituents which A may bear are not specifically defined. Methyl 2-(p-chlorophenylthio) acetate is prepared from methyl chloroacetate and sodium p-chlorothiophenate. Methyl 2-(p-aminophenylthio) acetate is prepared either by reduction of the corresponding nitro compound or by esterification, and is acetylated to methyl 2-(p-acetylaminophenylthio) acetate. Chloroacetyltrimethylhydrazine is prepared from trimethylhydrazine and chloroacetyl-chloride.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2443254A GB782420A (en) | 1954-08-23 | 1954-08-23 | New hydrazides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2443254A GB782420A (en) | 1954-08-23 | 1954-08-23 | New hydrazides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB782420A true GB782420A (en) | 1957-09-04 |
Family
ID=10211642
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2443254A Expired GB782420A (en) | 1954-08-23 | 1954-08-23 | New hydrazides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB782420A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1089768B (en) * | 1957-07-03 | 1960-09-29 | Hoffmann La Roche | Process for the preparation of substituted acid hydrazides |
US3065265A (en) * | 1957-07-04 | 1962-11-20 | Hoffmann La Roche | Amino acid hydrazides |
US3072713A (en) * | 1958-10-17 | 1963-01-08 | Hoffmann La Roche | N1-substituted benzoyl-n1, n2-di-isopropyl hydrazides |
US3209025A (en) * | 1960-10-29 | 1965-09-28 | Hoechst Ag | Bis-(beta-carbhydrazido-ethyl)-sulfone |
US3260746A (en) * | 1961-08-01 | 1966-07-12 | Ici Ltd | Bis-(n-acetylhydrazino-n'-carbonylmethyl)disulphide |
WO2001070685A3 (en) * | 2000-03-22 | 2003-03-27 | Solulink Inc | Hydrazine-based and carbonyl-based bifunctional crosslinking reagents |
WO2007062177A2 (en) * | 2005-11-23 | 2007-05-31 | Ventana Medical Systems, Inc. | Molecular conjugate |
WO2014022923A1 (en) * | 2012-08-10 | 2014-02-13 | Mcmaster University | Antibacterial inhibitors |
US8658389B2 (en) | 2005-04-28 | 2014-02-25 | Ventana Medical Systems, Inc. | Antibody conjugates |
-
1954
- 1954-08-23 GB GB2443254A patent/GB782420A/en not_active Expired
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1089768B (en) * | 1957-07-03 | 1960-09-29 | Hoffmann La Roche | Process for the preparation of substituted acid hydrazides |
US3065265A (en) * | 1957-07-04 | 1962-11-20 | Hoffmann La Roche | Amino acid hydrazides |
US3072713A (en) * | 1958-10-17 | 1963-01-08 | Hoffmann La Roche | N1-substituted benzoyl-n1, n2-di-isopropyl hydrazides |
US3209025A (en) * | 1960-10-29 | 1965-09-28 | Hoechst Ag | Bis-(beta-carbhydrazido-ethyl)-sulfone |
US3260746A (en) * | 1961-08-01 | 1966-07-12 | Ici Ltd | Bis-(n-acetylhydrazino-n'-carbonylmethyl)disulphide |
WO2001070685A3 (en) * | 2000-03-22 | 2003-03-27 | Solulink Inc | Hydrazine-based and carbonyl-based bifunctional crosslinking reagents |
US8658389B2 (en) | 2005-04-28 | 2014-02-25 | Ventana Medical Systems, Inc. | Antibody conjugates |
US11359185B2 (en) | 2005-04-28 | 2022-06-14 | Ventana Medical Systems, Inc. | Antibody conjugates |
US9315789B2 (en) | 2005-04-28 | 2016-04-19 | Ventana Medical Systems, Inc. | Antibody conjugates |
AU2006318438B2 (en) * | 2005-11-23 | 2011-09-22 | Ventana Medical Systems, Inc. | Molecular conjugate |
US8686122B2 (en) | 2005-11-23 | 2014-04-01 | Ventana Medical Systems, Inc. | Molecular conjugate |
CN101535244B (en) * | 2005-11-23 | 2014-07-23 | 文塔納医疗系统公司 | Molecular conjugate |
CN104090095A (en) * | 2005-11-23 | 2014-10-08 | 文塔纳医疗系统公司 | Molecular conjugate |
US9310373B2 (en) | 2005-11-23 | 2016-04-12 | Ventana Medical Systems, Inc. | Molecular conjugate |
WO2007062177A3 (en) * | 2005-11-23 | 2009-05-28 | Ventana Med Syst Inc | Molecular conjugate |
CN104090095B (en) * | 2005-11-23 | 2016-06-01 | 文塔纳医疗系统公司 | Molecular conjugate |
WO2007062177A2 (en) * | 2005-11-23 | 2007-05-31 | Ventana Medical Systems, Inc. | Molecular conjugate |
WO2014022923A1 (en) * | 2012-08-10 | 2014-02-13 | Mcmaster University | Antibacterial inhibitors |
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