(S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Base Information

• Chemical Name: (S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one
• CAS No.: 1360591-23-6
• Molecular Formula: C₂₂H₂₀ClF₃N₂O₂
• Molecular Weight: 436.861
• Mol file: 1360591-23-6.mol

Synonyms:(S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Chemical Property of (S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

There total 10 articles about (S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-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: 73.0%

C18H14ClF3N2O3 (1414889-36-3) + (cyclopropylmethyl)triphenylphosphonium bromide (14799-82-7) → (S,Z)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (1414889-37-4) + (S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (1360591-23-6)

Guidance literature:

(cyclopropylmethyl)triphenylphosphonium bromide; With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at 20 ℃; for 0.25h; Inert atmosphere;

C₁₈H₁₄ClF₃N₂O₃; In tetrahydrofuran; toluene; Overall yield = 82 %;

DOI:10.1039/c2cc36307k DOI:10.1039/c2cc36307k

Reference yield:

6-chloro-1-[(4-methoxyphenyl)methyl]-4-(trifluoromethyl)hydroquinazolin-2-one (497235-37-7) → (S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (1360591-23-6)

Guidance literature:

Multi-step reaction with 3 steps

1: C₂₉H₂₈F₆N₄OS / toluene / 24 h / 0 °C

2: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

3: lithium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

With C₂₉H₂₈F₆N₄OS; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene; 3: |Wittig Olefination;

DOI:10.1039/c2cc36307k DOI:10.1039/c2cc36307k

Reference yield:

(R)-6-chloro-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazoline-4-carbonitrile (1414889-08-9) → (S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (1360591-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

2: lithium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

With diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene; 2: |Wittig Olefination;

DOI:10.1039/c2cc36307k DOI:10.1039/c2cc36307k

upstream raw materials:

(R)-6-chloro-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazoline-4-carbonitrile

C₁₈H₁₄ClF₃N₂O₃

(cyclopropylmethyl)triphenylphosphonium bromide

6-chloro-1-[(4-methoxyphenyl)methyl]-4-(trifluoromethyl)hydroquinazolin-2-one

Downstream raw materials:

(S,E)-6-chloro-4-(2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one