4-Thiazolecarbonitrile, 2-(bromomethyl)-

Base Information

• Chemical Name: 4-Thiazolecarbonitrile, 2-(bromomethyl)-
• CAS No.: 454483-81-9
• Molecular Formula: C5H3BrN2S
• Molecular Weight: 203.062
• Mol file: 454483-81-9.mol

Synonyms:

Chemical Property of 4-Thiazolecarbonitrile, 2-(bromomethyl)-

Chemical Property:

• PSA: 64.92000
• LogP: 1.90968

Purity/Quality:

2-(Bromomethyl)thiazole-4-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-(Bromomethyl)thiazole-4-carbonitrile is an intermediate in preparation of 1,1-dioxido-4H-1,2,4-benzothiadiazines as hepatitis C polymerase inhibitors and anti-infective agents.

Technology Process of 4-Thiazolecarbonitrile, 2-(bromomethyl)-

There total 3 articles about 4-Thiazolecarbonitrile, 2-(bromomethyl)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

2-methylthiazol-4-carbonitrile (21917-76-0) → 2-(bromomethyl)-1,3-thiazole-4-carbonitrile (454483-81-9)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 95 ℃; for 15h;

Reference yield:

ethyl 2-methylthiazole-4-carboxylate (6436-59-5) → 2-(bromomethyl)-1,3-thiazole-4-carbonitrile (454483-81-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / aq. NH₃ / methanol / 16 h / 20 °C

2: 56 percent / SOCl₂; NMM / dimethylformamide / 5 h / 0 - 20 °C

3: 39 percent / NBS / CCl₄ / 80 °C

With 4-methyl-morpholine; ammonium hydroxide; N-Bromosuccinimide; thionyl chloride; In methanol; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(02)00129-4

Reference yield:

2-methylthiazole-4-carboxamide (31825-95-3) → 2-(bromomethyl)-1,3-thiazole-4-carbonitrile (454483-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / SOCl₂; NMM / dimethylformamide / 5 h / 0 - 20 °C

2: 39 percent / NBS / CCl₄ / 80 °C

With 4-methyl-morpholine; N-Bromosuccinimide; thionyl chloride; In tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(02)00129-4

upstream raw materials:

2-methylthiazol-4-carbonitrile

2-methylthiazole-4-carboxamide

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

2-(aminomethyl)-thiazole-4-carbonitrile

Refernces

• 1、 -. "Anti-infective agents". . . Retrieved 2008/06/13.
• 2、 Reiner, John E.,Siev, Daniel V.,Araldi, Gian-Luca,Cui, Jingrong Jean,Ho, Jonathan Z.,Reddy, Komandla Malla,Mamedova, Lala,Vu, Phong H.,Lee, Kuen-Shan S.,Minami, Nathaniel K.,Gibson, Tony S.,Anderson, Susanne M.,Bradbury, Annette E.,Nolan, Thomas G.,Semple, J. Edward. "Non-covalent thrombin inhibitors featuring P3-heterocycles with P1-monocyclic arginine surrogates". . p. 1203 - 1208. Retrieved 2007/10/03.