IP Library › Granted Patent US 11,814,358
Granted Patent B2
US 11,814,358 · App. 17/401,269 · Granted Nov 14, 2023

Process for the preparation of 4-amino-N-tert-butyl-4,5-dihydro-3-isopropyl-5-oxo-1H-1,2,4-triazole-1-carboxamide (Amicarbazone)

Inventors: Vic Prasad (Mumbai, IN); Tinker McBrayer (New York, NY); Leandro Alves (Brazil, BR); Luiz Campos (Brazil, BR); Raj Arora (Mumbai, IN); Raj Tiwari (Mumbai, IN)
Assignee: UPL LIMITED
C07D249/12
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,814,358
App. No.
17/401,269
Granted
Nov 14, 2023
Kind
B2
Abstract

The present invention relates to an improved process for the preparation of 4-amino-N-tert-butyl-4,5-dihydro-3-isopropyl-5-oxo-1H-1,2,4-triazole-1-carboxamide (Amicarbazone). The present invention more particularly relates to an improved process for the preparation of 4-amino-N-tert-butyl-4,5-dihydro-3-isopropyl-5-oxo-1H-1,2,4-triazole-1-carboxamide (Amicarbazone) by coupling of 4-Amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-one (TAZ) and poor quality tert-Butyl isocyanate (TBIC) with purity less than or equal to 98%, preferably less than or equal to 85%.

Claims (14)

1. A method for the preparation of Amicarbazone comprising reacting 4-Amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-one (TAZ) with tert-Butyl isocyanate (TBIC) having low purity to form Amicarbazone,

wherein said low purity TBIC has a purity of less than or equal to 85%, and

wherein 18% or more molar excess of TBIC with respect to TAZ is used.

2. The process according to claim 1 , comprising:

a) preparing a solution of TAZ, potassium hydroxide, and toluene;

b) raising the temperature of the solution obtained in step (a) to the range of 50° C. to 70° C.;

c) adding the low purity TBIC without distillation to the solution of step (b);

d) heating the solution obtained in step c) at temperature in the range of 60° C. to 75° C.; and

e) cooling the solution obtained in step (d) to form the Amicarbazone.

3. The process as claimed in claim 2 , wherein the solution in step (e) is cooled to the temperature in the range of 40° C. to 50° C.

4. The process as claimed in claim 2 , wherein the cooled solution of step e) is optionally seeded with Amicarbazone.

5. The process as claimed in claim 1 , wherein the TBIC has a purity equal to or less than 80%.

6. The process as claimed in claim 1 , wherein the molar excess of TBIC with respect to TAZ is in the range of 18% to 22%.

7. The process as claimed in claim 2 , wherein the purity of Amicarbazone obtained in step (e) is more than 97%.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2022
From: PRASAD, VIC; MCBRAYER, TINKER; ALVES, LEANDRO; CAMPOS, LUIZ; ARORA, RAJ; TIWARI, RAJ
To: UPL LIMITED
Reel/Frame 060740/0841 →
Priority Claims (1)
IN 202021034703 · Aug 12, 2020 · national
Continuity (1)
Related Publication 20220177436A1 · Jun 9, 2022