3-Benzylcarbazic acid methyl ester

Base Information

• Chemical Name: 3-Benzylcarbazic acid methyl ester
• CAS No.: 69353-11-3
• Molecular Formula: C9H12N2O2
• Molecular Weight: 180.206
• Hs Code.: 2928000090
• Mol file: 69353-11-3.mol

Synonyms:Carbamic acid,benzylamino-,methyl ester;N1-benzyl-N2-methoxycarbonylhydrazine;Methyl 3-benzylcarbazate;CARBAZIC ACID,3-BENZYL-,METHYL ESTER;methyl N2-benzyl carbazate;methyl 2-benzylhydrazinecarboxylate;2-Benzyl-1-methoxycarbonyl-hydrazin;

Chemical Property of 3-Benzylcarbazic acid methyl ester

Chemical Property:

• PSA: 53.85000
• Density: 1.127g/cm³
• LogP: 1.64250
• Solubility.: DMSO; Chloroform; Ethyl Acetate; Ethanol

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 2-benzylhydrazinecarboxylate is an intermediate for the synthesis of CFM 1571 Hydrochloride (C291720), which acts as a soluble guanylyl cyclase (sGC) activator while ignoring adenylyl cyclase. Inhibits collagen-stimulated platelet aggregation in vitro.

Technology Process of 3-Benzylcarbazic acid methyl ester

There total 4 articles about 3-Benzylcarbazic acid methyl ester 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: 73.0%

methyl 3-benzylidenecarbazate (21732-13-8) → N1-benzyl-N2-methoxycarbonylhydrazine (69353-11-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 1.5h;

DOI:10.1021/ol203072u

Reference yield: 22.0%

hydrazinecarboxylic acid methyl ester (6294-89-9) + benzyl chloride (100-44-7) → N1-benzyl-N2-methoxycarbonylhydrazine (69353-11-3)

Guidance literature:

With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1055/s-0034-1379974

Reference yield:

benzaldehyde (100-52-7) → N1-benzyl-N2-methoxycarbonylhydrazine (69353-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / methanol / 25 - 65 °C / Molecular sieve

2: palladium 10% on activated carbon; hydrogen / methanol / 20 - 25 °C

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol;

DOI:10.1021/jm400923s

upstream raw materials:

hydrazinecarboxylic acid methyl ester

benzaldehyde

methyl 3-benzylidenecarbazate

benzyl chloride

Downstream raw materials:

2-methoxy-5-phenyl-1,3,4-oxadiazole

methyl 3-benzylidenecarbazate

methyl 2-benzyl-2-(3-phenylnaphthalen-1-yl)hydrazinecarboxylate

methyl 2-benzyl-3-isopropyl-4-propyl-2,3-dihydro-1H-benzo[g]indazole-1-carboxylate

Refernces

• 1、 Shang, Zhenhua,Chu, Qianqian,Tan, Sheng. "Metal-Free Synthesis of 1,3,4-Oxadiazoles from N′-(Arylmethyl)hydrazides or 1-(Arylmethyl)-2-(arylmethylene)hydrazines". supporting information. p. 1032 - 1040. Retrieved 2015/03/30.
• 2、 Suzuki, Yamato,Naoe, Saori,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki. "Gold-catalyzed three-component annulation: Efficient synthesis of highly functionalized dihydropyrazoles from alkynes, hydrazines, and aldehydes or ketones". supporting information; experimental part. p. 326 - 329. Retrieved 2012/02/15.