2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate

Base Information

• Chemical Name: 2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate
• CAS No.: 99924-11-5
• Molecular Formula: C₂₁H₂₀ClNO₅S
• Molecular Weight: 433.913
• Mol file: 99924-11-5.mol

Synonyms:2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate

Chemical Property of 2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate

There total 6 articles about 2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate 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: 83.0%

2-[2-(4-chlorophenyl)-5-(thien-3-yl)-4-oxazolyl]acetic acid (85162-14-7) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0) → 2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate (99924-11-5)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1021/jm00153a006

Reference yield:

4-chloro-benzoyl chloride (122-01-0) → 2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate (99924-11-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / aq. NaHCO₃ / ethyl acetate / Ambient temperature

2: 1.) NaH / 1.) DMF, -50 - -40 deg C, 15 min, 2.) DMF, from -50 to 0 deg C, 30 min

3: 78 percent / POCl₃ / dimethylformamide / 8 h / 20 - 25 °C

4: 89 percent / aq. KOH / methanol / 24 h / Ambient temperature

5: 83 percent / 1-methyl-2-chloropyridinium iodide (MCPI), Et₃N / tetrahydrofuran / 18 h / Ambient temperature

With potassium hydroxide; 2-chloro-1-methyl-pyridinium iodide; sodium hydride; sodium hydrogencarbonate; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00153a006

Reference yield:

N-(4-chlorobenzoyl)aminomethyl(3-thienyl)ketone (85210-63-5) → 2,2-dimethyl-1,3-dioxolanylmethyl 2-(4-chlorophenyl)-5-(3-thienyl)-4-oxazoleacetate (99924-11-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, -50 - -40 deg C, 15 min, 2.) DMF, from -50 to 0 deg C, 30 min

2: 78 percent / POCl₃ / dimethylformamide / 8 h / 20 - 25 °C

3: 89 percent / aq. KOH / methanol / 24 h / Ambient temperature

4: 83 percent / 1-methyl-2-chloropyridinium iodide (MCPI), Et₃N / tetrahydrofuran / 18 h / Ambient temperature

With potassium hydroxide; 2-chloro-1-methyl-pyridinium iodide; sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00153a006

upstream raw materials:

2-[2-(4-chlorophenyl)-5-(thien-3-yl)-4-oxazolyl]acetic acid

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol

4-chloro-benzoyl chloride

N-(4-chlorobenzoyl)aminomethyl(3-thienyl)ketone

Refernces