5-(Hydroxymethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one

Base Information

• Chemical Name: 5-(Hydroxymethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one
• CAS No.: 84460-41-3
• Molecular Formula: C₁₀H₁₀INO₃
• Molecular Weight: 319.099
• DSSTox Substance ID: DTXSID60401776
• Mol file: 84460-41-3.mol

Synonyms:84460-41-3;5-Hydroxymethyl-3-(4-iodophenyl)-2-oxazolidinone;5-(hydroxymethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one;5-(Hydroxymethyl)-3-(4-iodophenyl)oxazolidin-2-one;SCHEMBL3426022;DTXSID60401776;MFCD03426269;AKOS022172844;A915029

Chemical Property of 5-(Hydroxymethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one

Chemical Property:

• Vapor Pressure: 2.22E-07mmHg at 25°C
• Boiling Point: 407.7°C at 760 mmHg
• PKA: 14.05±0.10(Predicted)
• Flash Point: 200.4°C
• PSA: 49.77000
• Density: 1.853g/cm³
• LogP: 1.67370
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 318.97054
• Heavy Atom Count: 15
• Complexity: 241

Purity/Quality:

98%min ^*data from raw suppliers

5-Hydroxymethyl-3-(4-iodophenyl)-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(=O)N1C2=CC=C(C=C2)I)CO
• Uses: 5-Hydroxymethyl-3-(4-iodophenyl)-2-oxazolidinone was used as a reactant in the synthesis of 5-(Aminomethyl)oxazolidine dericatives, some of which inhibited monoamine oxidase type B enzyme in rats.

Technology Process of 5-(Hydroxymethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one

There total 8 articles about 5-(Hydroxymethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one 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: 89.0%

carbon dioxide (124-38-9,18923-20-1) + 1-chloro-3-[(4-iodophenyl)amino]propan-2-ol (4643-46-3) → 5-(hydroxymethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one (84460-41-3)

Guidance literature:

With tetrabutylammomium bromide; caesium carbonate; In methanol; at 50 ℃; for 24h;

DOI:10.1039/d1cc02493k

Reference yield: 82.0%

carbon dioxide (124-38-9,18923-20-1) + C9H10INO → 5(R)-Hydroxymethyl-3-(4-iodophenyl)oxazolidin-2-one (252330-13-5,84460-41-3)

Guidance literature:

With dmap; C₂₀H₁₄AlNO₃; In dichloromethane; at 25 ℃; for 60h; under 760.051 Torr; stereoselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.8b02186

Reference yield: 68.0%

(S)‐3‐[(4‐iodophenyl)amino]propane‐1,2‐diol + Diethyl carbonate (105-58-8,76619-83-5) → (S)‐5‐(hydroxymethyl)‐3‐(4‐iodophenyl)oxazolidin‐2‐one (84460-41-3)

Guidance literature:

With sodium methylate; In methanol; toluene; at 105 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ardp.201900129

upstream raw materials:

carbon dioxide

p-aminoiodobenzene

Diethyl carbonate

1-chloro-3-[(4-iodophenyl)amino]propan-2-ol

Refernces

• 1、 Ding, Shi,Ji, Jing-Chao,Zhang, Ming-Juan,Yang, Yu-She,Wang, Rui,Zhu, Xing-Long,Wang, Li-Hong,Zhong, Yi,Gao, Le,Lu, Man,Liu, Ju,Chen, Ye. "Exploration of the structure–activity relationship and druggability of novel oxazolidinone-based compounds as Gram-negative antibacterial agents". . . Retrieved 2019/09/06.
• 2、 -. "Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them". . . Retrieved 2008/06/13.