3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine

Base Information

• Chemical Name: 3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine
• CAS No.: 36884-21-6
• Molecular Formula: C₁₆H₁₇NO₄S
• Molecular Weight: 319.381
• Mol file: 36884-21-6.mol

Synonyms:3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine

Chemical Property of 3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine

There total 4 articles about 3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine 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: 88.0%

4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-3-carboxylic acid (35970-38-8) → 3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine (36884-21-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 50 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00352

Reference yield:

2-amino-phenol (95-55-6) → 3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine (36884-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 24 h / 60 °C

2.1: magnesium / methanol / 12 h / 40 °C

3.1: 2,5-Dimethyl-1,4-benzoquinone; palladium diacetate; oxygen / dimethyl sulfoxide / 24 h / 70 °C / Sealed tube

4.1: ruthenium trichloride; water / acetonitrile; tetrachloromethane / 0.5 h / 20 °C

4.2: 12 h / 40 °C

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 50 °C / Inert atmosphere

With pyridine; ruthenium trichloride; lithium aluminium tetrahydride; 2,5-Dimethyl-1,4-benzoquinone; water; oxygen; palladium diacetate; magnesium; In tetrahydrofuran; methanol; tetrachloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/acs.orglett.8b00352

Reference yield:

N-acetyl-2-(2,3-epoxypropoxy)aniline (57682-11-8) → 3-hydroxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine (36884-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide / Ambient temperature

2: Py

With pyridine; sodium hydride; In N,N-dimethyl-formamide;

upstream raw materials:

2,3-dihydro-3-hydroxymethyl-[1,4]benzoxazine

p-toluenesulfonyl chloride

N-acetyl-2-(2,3-epoxypropoxy)aniline

4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-3-carboxylic acid