GB1285390A - Improvements in the n-alkylation of acylated amino compounds - Google Patents
Improvements in the n-alkylation of acylated amino compoundsInfo
- Publication number
- GB1285390A GB1285390A GB6045370A GB6045370A GB1285390A GB 1285390 A GB1285390 A GB 1285390A GB 6045370 A GB6045370 A GB 6045370A GB 6045370 A GB6045370 A GB 6045370A GB 1285390 A GB1285390 A GB 1285390A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkylation
- compounds
- sulphate
- dmso
- reacted
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title abstract 3
- 238000005804 alkylation reaction Methods 0.000 title abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 9
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 4
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 abstract 2
- 238000007126 N-alkylation reaction Methods 0.000 abstract 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 2
- WPNMLCMTDCANOZ-UHFFFAOYSA-N [5-chloro-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WPNMLCMTDCANOZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229940100198 alkylating agent Drugs 0.000 abstract 2
- 239000002168 alkylating agent Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical group NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 abstract 1
- ZPVQUACUWKFQRQ-UHFFFAOYSA-N 3-(methylamino)-5-nitrobenzoic acid Chemical compound CNC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 ZPVQUACUWKFQRQ-UHFFFAOYSA-N 0.000 abstract 1
- PXAFGNQRBIXGLM-UHFFFAOYSA-N 3-acetamido-5-nitrobenzoic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 PXAFGNQRBIXGLM-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- GSHZFWDWLSHGCQ-UHFFFAOYSA-N CS(=O)CC.CS(=O)C Chemical compound CS(=O)CC.CS(=O)C GSHZFWDWLSHGCQ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- AGKPGIOZNCJFTQ-UHFFFAOYSA-N [2-(methylamino)phenyl]-phenylmethanone Chemical class CNC1=CC=CC=C1C(=O)C1=CC=CC=C1 AGKPGIOZNCJFTQ-UHFFFAOYSA-N 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- HDIPZJLCVODIRC-UHFFFAOYSA-N n-benzyl-n-ethylacetamide Chemical compound CCN(C(C)=O)CC1=CC=CC=C1 HDIPZJLCVODIRC-UHFFFAOYSA-N 0.000 abstract 1
- UZJLYRRDVFWSGA-UHFFFAOYSA-N n-benzylacetamide Chemical compound CC(=O)NCC1=CC=CC=C1 UZJLYRRDVFWSGA-UHFFFAOYSA-N 0.000 abstract 1
- QKIDBCKIVIQWLL-UHFFFAOYSA-N n-methyl-n-(2-methylphenyl)acetamide Chemical compound CC(=O)N(C)C1=CC=CC=C1C QKIDBCKIVIQWLL-UHFFFAOYSA-N 0.000 abstract 1
- LMTGCJANOQOGPI-UHFFFAOYSA-N n-methyl-n-phenylacetamide Chemical compound CC(=O)N(C)C1=CC=CC=C1 LMTGCJANOQOGPI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1785969 | 1969-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1285390A true GB1285390A (en) | 1972-08-16 |
Family
ID=20304064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6045370A Expired GB1285390A (en) | 1969-12-23 | 1970-12-21 | Improvements in the n-alkylation of acylated amino compounds |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH520108A (enrdf_load_stackoverflow) |
| DE (1) | DE2063017A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2081393B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1285390A (enrdf_load_stackoverflow) |
| NL (1) | NL7018733A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2012029672A1 (ja) * | 2010-08-31 | 2013-10-28 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | 有害生物防除剤 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2436774A1 (fr) * | 1978-09-20 | 1980-04-18 | Fabre Sa Pierre | Procede de preparation de n-alcoylamino benzophenones |
| FR2436776A1 (fr) * | 1978-09-25 | 1980-04-18 | Fabre Sa Pierre | Nouveaux derives d'ortho chloro benzoyl-2 chloro-4 glycylanilide, leur preparation et leur application en tant que medicaments |
| DE2919755A1 (de) | 1979-05-16 | 1980-11-27 | Hoechst Ag | Verfahren zur herstellung von n-vinyl- n-alkyl-carbonsaeureamiden |
| DE2944456C2 (de) * | 1979-11-03 | 1982-04-01 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von N-α -Alkoxyalkyl-carbonsäureamiden |
| GB2092136B (en) * | 1981-01-17 | 1985-06-05 | Mitsui Toatsu Chemicals | Production of n-substituted amide compounds |
-
1970
- 1970-12-21 FR FR7045996A patent/FR2081393B1/fr not_active Expired
- 1970-12-21 GB GB6045370A patent/GB1285390A/en not_active Expired
- 1970-12-22 DE DE19702063017 patent/DE2063017A1/de active Pending
- 1970-12-23 CH CH1911770A patent/CH520108A/fr not_active IP Right Cessation
- 1970-12-23 NL NL7018733A patent/NL7018733A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2012029672A1 (ja) * | 2010-08-31 | 2013-10-28 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | 有害生物防除剤 |
| US9328068B2 (en) | 2010-08-31 | 2016-05-03 | Meiji Seika Pharma Co., Ltd. | N-[1-((6-chloropyridin-3-yl) methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of animal parasitic pests and agricultural/horticultural pests |
| US9717242B2 (en) | 2010-08-31 | 2017-08-01 | Meiji Seika Pharma Co., Ltd. | N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of agricultural/horticultural pests |
| US10085449B2 (en) | 2010-08-31 | 2018-10-02 | Meiji Seika Pharma Co., Ltd. | N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2- trifluoroacetamide for control of agricultural/horticultural pests |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7018733A (enrdf_load_stackoverflow) | 1971-06-25 |
| FR2081393A1 (enrdf_load_stackoverflow) | 1971-12-03 |
| DE2063017A1 (enrdf_load_stackoverflow) | 1972-10-05 |
| CH520108A (fr) | 1972-03-15 |
| FR2081393B1 (enrdf_load_stackoverflow) | 1974-08-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |