# US 11,440,890 B2 · Manufacturing process for 2-nitroimino heterocyclic compounds

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- Number: US 11,440,890 B2
- Document ID: US11440890B2
- Status: Granted
- Kind: B2
- Application number: 17/272,712
- Filed: 2019-09-11
- Published: 2021-07-15
- Granted: 2022-09-13
- Earliest claimed: 2018-09-17
- Assignees: Upl Ltd
- Applicants: Upl Ltd
- Inventors: Chandrasekhar Dayal Mudaliar; Sadanand Sadashiv Pandit; Jaidev Rajnikant Shroff; Vikram Rajnikant Shroff
- Web page: https://patentgrep.com/patent/US11440890B2

## CPC

- C07D 233/52: with hetero atoms directly attached to said nitrogen atoms
- C07D 239/12: Nitrogen atoms not forming part of a nitro radical
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to a process for manufacture of 2-nitroimino heterocyclic compounds and intermediates thereof. More particularly, the present invention relates to a convenient manufacturing process for preparation of 2-nitroimino imidazolidine compounds.

## Claims

### Claim 1

A process for preparation of a nitroimino heterocyclic compound of Formula B:
comprising reacting a compound of Formula II;
with a compound of Formula III
wherein R represents hydrogen or an optionally substituted lower alkyl of 1 to 4 carbon atoms; and n is 2, 3 or 4;
wherein said compound of formula II is reacted with said compound of formula III without isolating or separating the compound of formula II from a mixture comprising the reaction product of a reaction of a compound of formula I with an acid

### Claim 2 (depends on 1)

The process as claimed in claim 1, wherein said nitroimino heterocyclic compound of Formula B is prepared using a diamine of Formula III wherein n is 2.

### Claim 3 (depends on 1)

The process as claimed in claim 1, wherein said nitroimino heterocyclic compound of Formula B is prepared using a diamine of Formula III wherein n is 3.

### Claim 4 (depends on 1)

The process as claimed in claim 1, wherein said compound of formula B is selected from

### Claim 5 (depends on 1)

The process as claimed in claim 1, wherein said acid is sulfuric acid.

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein the reaction proceeds without isolation of the compound of Formula II.

### Claim 7 (depends on 1)

The process as claimed in claim 1, wherein the reaction is carried out at a temperature in the range of about of 5° C. to about 50° C.

### Claim 8

A one pot process for preparing a nitroimino heterocyclic compound of Formula B
comprising:
a) reacting a compound of Formula I with an acid to form a compound of Formula II; and
b) reacting compound of Formula II with a compound of Formula III to give a compound of Formula B, wherein compound of formula II is not isolated,
and wherein R represents hydrogen or an optionally substituted lower alkyl of 1 to 4 carbon atoms and n is 2, 3 or 4.

### Claim 9 (depends on 6)

The process as claimed in claim 6, wherein said nitroimino heterocyclic compounds of Formula B is a compound of formula IV

### Claim 10

A process for preparing a nitroimino heterocyclic compound of Formula IV:
said process comprising reacting a compound of Formula II with ethylene diamine to obtain a compound of formula IV:
wherein said compound of formula II is reacted with ethylene diamine without isolating or separating the compound of formula II from a mixture comprising the reaction product of a reaction of a compound of formula I with an acid:

### Claim 11

A one pot process for preparing compound of Formula IV,
comprising:
a) treating a compound of Formula I with sulfuric acid to form a compound of Formula II; and
b) treating a compound of Formula II with ethylene diamine to give a compound of Formula IV, wherein compound of Formula II is not isolated

### Claim 12 (depends on 4)

The process of claim 4, further comprising
reacting the compound of Formula IV with a compound of Formula V to obtain imidacloprid;

### Claim 13 (depends on 10)

The process of claim 10, further comprising
reacting the compound of Formula IV with a compound of Formula V to obtain imidacloprid;

### Claim 14 (depends on 13)

The process of claim 13, wherein the process is a one pot process for preparing imidacloprid.