5-(3-Methyl-3-methylthio-2-oxo-1H-indol-5-yl)-3,6-dihydro-1,3,4-thiadiazin-2-one

Base Information

• Chemical Name: 5-(3-Methyl-3-methylthio-2-oxo-1H-indol-5-yl)-3,6-dihydro-1,3,4-thiadiazin-2-one
• CAS No.: 122280-58-4
• Molecular Formula: C₁₃H₁₃N₃O₂S₂
• Molecular Weight: 307.397
• DSSTox Substance ID: DTXSID10924127
• Nikkaji Number: J442.964H
• ChEMBL ID: CHEMBL295366
• Mol file: 122280-58-4.mol

Synonyms:5-(3,6-dihydro-2-oxo-2H-1,3,4-thiadiazin-5-yl)-1,3-dihydro-3- methyl-3-methylthio-2H-indol-2-one;5-DOTMM-indol-2-one

Chemical Property of 5-(3-Methyl-3-methylthio-2-oxo-1H-indol-5-yl)-3,6-dihydro-1,3,4-thiadiazin-2-one

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 128.14000
• Density: 1.55g/cm³
• LogP: 1.53810
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 307.04491901
• Heavy Atom Count: 20
• Complexity: 482

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=C(C=CC(=C2)C3=NNC(=O)SC3)NC1=O)SC

Technology Process of 5-(3-Methyl-3-methylthio-2-oxo-1H-indol-5-yl)-3,6-dihydro-1,3,4-thiadiazin-2-one

There total 5 articles about 5-(3-Methyl-3-methylthio-2-oxo-1H-indol-5-yl)-3,6-dihydro-1,3,4-thiadiazin-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: 41.0%

5-<(2-bromo-1-oxo)ethyl>-1,3-dihydro-3-methyl-3-methylthio-2H-indol-2-one (122281-01-0) + methyl imidothiocarbamate (19692-07-0) → 1,3-dihydro-5-(3,6-dihydro-2-oxo-2H-1,3,4-thiadiazin-5-yl)-3-methyl-3-(methylthio)-2H-indol-2-one (122280-58-4)

Guidance literature:

In acetonitrile; for 2h; Heating;

DOI:10.1002/jhet.5570280609

Reference yield:

5-<(2-bromo-1-oxo)ethyl>-1,3-dihydro-3-methyl-3-methylthio-2H-indol-2-one (122281-01-0) → 1,3-dihydro-5-(3,6-dihydro-2-oxo-2H-1,3,4-thiadiazin-5-yl)-3-methyl-3-(methylthio)-2H-indol-2-one (122280-58-4)

Guidance literature:

In acetonitrile;

Reference yield:

p-aminobenzophenone (99-92-3) → 1,3-dihydro-5-(3,6-dihydro-2-oxo-2H-1,3,4-thiadiazin-5-yl)-3-methyl-3-(methylthio)-2H-indol-2-one (122280-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) t-BuOCl / 1) CH₂Cl₂, -65 deg C, 10 min, 2) CH₂Cl₂, -65 deg C, 1h

2: 85 percent / 2M aq. HCl / 2 h / Ambient temperature

3: 64 percent / Br₂ / CHCl₃ / 0.25 h / 0 - 5 deg C to RT

4: 41 percent / acetonitrile / 2 h / Heating

With hydrogenchloride; tert-butylhypochlorite; bromine; In chloroform; acetonitrile;

DOI:10.1002/jhet.5570280609

upstream raw materials:

5-<(2-bromo-1-oxo)ethyl>-1,3-dihydro-3-methyl-3-methylthio-2H-indol-2-one

methyl imidothiocarbamate

p-aminobenzophenone

1,3-dihydro-3-methyl-3-methylthio-5-(1-oxoethyl-2H-indol-2-one)