GB2119791A - Aziridine derivative - Google Patents
Aziridine derivative Download PDFInfo
- Publication number
- GB2119791A GB2119791A GB08310523A GB8310523A GB2119791A GB 2119791 A GB2119791 A GB 2119791A GB 08310523 A GB08310523 A GB 08310523A GB 8310523 A GB8310523 A GB 8310523A GB 2119791 A GB2119791 A GB 2119791A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- aziridine
- nitromethylene
- methyl
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/12—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Abstract
The aziridine derivative N-methyl- alpha -(nitromethylene)-1-aziridine- methanamine is a useful intermediate for use in the preparation of ranitidine.
Description
SPECIFICATION
Aziridine derivative
This invention relates to an aziridine derivative.
The furan derivative of formula (I)
which is known as ranitidine is disclosed in British
Patent Specification No. 1 565966 as a potent and selective H2-antagonist.
Our British Patent application No. 81 00477 (publication No. 2067991A) describes and ciaims a process for the preparation of the furan derivative of formula (I) which comprises reacting a thiol of formula (II)
with an alkylating agent of formula (III)
where R1 is the group -CH2OH 2L, in which L is a leaving group, and R2 is a hydrogen atom, or R, and R2, together with the nitrogen atom to which they are attached, form an ethyleneimino group.
This process is a novel and useful method for the preparation of the compound ranitidine.
The present invention provides the compound defined by formula (III) above in which R,R2N is an ethyleneimino group, i.e. N-methyl-a- (nitromethylene)- 1 -aziridinemethanamine of formula (IV)
The aziridine derivative of formula (IV) may be prepared by reaction of ethyleneimine with a nitroethenamine of formula (V)
in which L" is a leaving group, for example a C14 alkoxy group or a C1 < alkylthio group, preferably methylthio. The reaction may be carried out in a suitable aprotic solvent such as acetonitrile.
The invention is illustrated by the following example:
Example N-Methyl-a-(nitromethylene)- 1 -aziridinemethanamine
A solution of ethyleneimine (0.47 g) and N ethyl(1 -methylthio)-2-nitroetheneamine (1.48 g) in acetonitrile (5 ml) was stirred at room temperature for 2 days. The suspension was evaporated in vacuo at room temperature and the residue extracted with hot ethyl acetate (100 ml).
Evaporation of the extract in vacuo gave a residue which was suspended in ethyl acetate (50 ml) and filtered. The filtrate was evaporated to ca. 5 ml and chromatographed (silica/ethyl acetate). The appropriate eluate [TLC (silica/ethyl acetate) Rf 0.28] was evaporated in vacuo to give the title compound (0.33 g), m.p. 1181190.
Claims
1. N-Methyl-a-(nitromethylene)-1-aziridine- methanamine.
2. A process for the preparation of N-methyl-a- (nitromethylene)- 1 -aziridine-methanamine which comprises reacting ethyleneimine with a nitroethenamine of formula (V)
where L" is a leaving group.
3. A process as claimed in claim 2 wherein L" is a C,, alkoxy group or a C14 alkylthio group.
4. A process for the preparation of N-methyl-a- (nitromethylene)-1 -aziridine-methanamine substantially as described with particular reference to the example.
5. N-Methyl-a-(nitromethylene)-1 -aziridine- methanamine when prepared by a process as claimed in any of claims 2 to 4.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (5)
1. N-Methyl-a-(nitromethylene)-1-aziridine- methanamine.
2. A process for the preparation of N-methyl-a- (nitromethylene)- 1 -aziridine-methanamine which comprises reacting ethyleneimine with a nitroethenamine of formula (V)
where L" is a leaving group.
3. A process as claimed in claim 2 wherein L" is a C,, alkoxy group or a C14 alkylthio group.
4. A process for the preparation of N-methyl-a- (nitromethylene)-1 -aziridine-methanamine substantially as described with particular reference to the example.
5. N-Methyl-a-(nitromethylene)-1 -aziridine- methanamine when prepared by a process as claimed in any of claims 2 to 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08310523A GB2119791B (en) | 1980-01-08 | 1983-04-19 | Aziridine derivative |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8000580 | 1980-01-08 | ||
| GB08310523A GB2119791B (en) | 1980-01-08 | 1983-04-19 | Aziridine derivative |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8310523D0 GB8310523D0 (en) | 1983-05-25 |
| GB2119791A true GB2119791A (en) | 1983-11-23 |
| GB2119791B GB2119791B (en) | 1984-05-31 |
Family
ID=26274064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08310523A Expired GB2119791B (en) | 1980-01-08 | 1983-04-19 | Aziridine derivative |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2119791B (en) |
-
1983
- 1983-04-19 GB GB08310523A patent/GB2119791B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2119791B (en) | 1984-05-31 |
| GB8310523D0 (en) | 1983-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940108 |