(+)-Mephobarbitol

Base Information

• Chemical Name: (+)-Mephobarbitol
• CAS No.: 2671-99-0
• Molecular Formula: C13H14 N2 O3
• Molecular Weight: 246.2619
• DSSTox Substance ID: DTXSID50181212
• Nikkaji Number: J367.448G
• Wikidata: Q83051821
• ChEMBL ID: CHEMBL399103
• Mol file: 2671-99-0.mol

Synonyms:(+)-Mephobarbitol;2671-99-0;(S)-5-Ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione;2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl-, (S)-;(S)-Mephobarbital;( )-Mephobarbitol;SCHEMBL35625;CHEMBL399103;DTXSID50181212;5-ethyl-1-methyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-\ trione

Chemical Property of (+)-Mephobarbitol

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.211g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 246.10044231
• Heavy Atom Count: 18
• Complexity: 388

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C(=O)NC(=O)N(C1=O)C)C2=CC=CC=C2
• Isomeric SMILES: CC[C@@]1(C(=O)NC(=O)N(C1=O)C)C2=CC=CC=C2

Technology Process of (+)-Mephobarbitol

There total 5 articles about (+)-Mephobarbitol 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:

(5R)-5-ethyl-3-methyl-1-(methyl β-D-glucopyranosyluronate)-5-phenyl-2,4,6-(1H,3H,5H)-pyrimidinetrione (165131-09-9) → (+)-Mephobarbital (2671-99-0)

Guidance literature:

With sodium dichromate; sulfuric acid; at 93 ℃; for 0.75h; Yield given;

DOI:10.1016/0008-6215(94)00358-M

Reference yield:

5-Ethyl-5-phenyl-2,4,6-tris-trimethylsilanyloxy-4,5-dihydro-pyrimidine → (+)-Mephobarbital (2671-99-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 36 percent / CF₃SO₃SiMe₃ / 1,2-dichloro-ethane / 18 h / Ambient temperature

2: conc. HCl / methanol / 5 h / 50 °C

3: ethanol; diethyl ether / 0.33 h / Ambient temperature

4: Na₂Cr₂O₇, H₂SO₄ / 0.75 h / 93 °C

With hydrogenchloride; sodium dichromate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; In methanol; diethyl ether; ethanol; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(94)00358-M

Reference yield:

5-ethyl-1-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-5-phenyl-2,4,6-(1H,3H,5H)-pyrimidinetrione → (+)-Mephobarbital (2671-99-0)

Guidance literature:

Multi-step reaction with 3 steps

1: conc. HCl / methanol / 5 h / 50 °C

2: ethanol; diethyl ether / 0.33 h / Ambient temperature

3: Na₂Cr₂O₇, H₂SO₄ / 0.75 h / 93 °C

With hydrogenchloride; sodium dichromate; sulfuric acid; In methanol; diethyl ether; ethanol;

DOI:10.1016/0008-6215(94)00358-M

upstream raw materials:

(5R)-5-ethyl-3-methyl-1-(methyl β-D-glucopyranosyluronate)-5-phenyl-2,4,6-(1H,3H,5H)-pyrimidinetrione

mephobarbital

(5R)-5-ethyl-1-(methyl β-D-glucopyranosyluronate)-5-phenyl-2,4,6-(1H,3H,5H)-pyrimidinetrione

Downstream raw materials:

(-)-Mephenytoin

Refernces

• 1、 Neighbors, Suzanne M.,Soine, William H.,Paibir, Sheela G.. "Synthesis of N-β-D-glucopyranosyluronate derivatives of barbital, phenobarbital, metharbital, and mephobarbital". . p. 259 - 272. Retrieved 2007/10/02.