6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

Base Information

• Chemical Name: 6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one
• CAS No.: 177530-93-7
• Deprecated CAS: 154635-17-3
• Molecular Formula: C14H9ClF3NO2
• Molecular Weight: 315.679
• Hs Code.: 2934990002
• DSSTox Substance ID: DTXSID00861416
• Nikkaji Number: J3.113.316E
• ChEMBL ID: CHEMBL59507
• Mol file: 177530-93-7.mol

Synonyms:Rac-Efavirenz;177530-93-7;6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one;154635-17-3;Efavirenz Racemic;L 741211;6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one;rac Efavirenz-d4;Efavirenz-13C6;rac Efavirenz-d5 (major);6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one;L741211;2H-3,1-Benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-;6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-3-one;6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one;SMR000718784;L-741211;C14-H9-Cl-F3-N-O2;MFCD05662344;Racemic-Efavirenz;NCGC00159337-02;1246812-58-7;Efavirenz [racemic];(+/-)-Efavirenz;Efavirenz Racemic (20mg);6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1H-benzo[d][1,3]oxazin-2(4H)-one;MLS001304019;MLS006011825;CHEMBL59507;SCHEMBL464769;DTXSID00861416;2h-3,1-benzoxazin-2-ona, 6-cloro-4-(2-ciclopropiletinil)-1,4-dihidro-4-(trifluorometil)-;HMS2231D09;HMS3373J19;2H-3,1-Benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4S)-;Tox21 111582;BBL010771;STK582240;STL454184;AKOS005506207;NCGC00159337-03;NCGC00159337-06;SY009682;VS-02672;LS-173466;FT-0625647;FT-0667824;AB00876268-06;L 743,726;(+) 6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl- 1,4-dihydro-2H-3,1-benzoxazin-2-one;(+) 6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one;(+/-) 6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one;(+/-)6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one;6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one;6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one;6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-4H-3,1-benzoxazin-2-ol;(S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one;2H-3,1-Benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (+-)-;((+/-)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one)

Chemical Property of 6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

Chemical Property:

• Melting Point: 107-109oC
• PSA: 41.82000
• LogP: 3.52230
• Storage Temp.: -20°C Freezer
• Solubility.: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 315.0273907
• Heavy Atom Count: 21
• Complexity: 519

Purity/Quality:

97% ^*data from raw suppliers

rac Efavirenz ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C#CC2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F
• Uses: rac Efavirenz is a mixture of both enantiomers for Efavirenz (E425000), a nonnucleoside HIV-1 reverse transcriptase inhibitor. Antiviral.

Technology Process of 6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

There total 15 articles about 6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-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: 95.0%

tert-butyl 4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenylcarbamate (201218-08-8) → rac-efavirenz (177530-93-7,154635-17-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; toluene; at 0 ℃; for 1h; Inert atmosphere; Reflux;

Reference yield: 40.0%

carbamic acid cyclopropyl-(2,5-dichloro-phenyl)-trifluoromethyl-prop-2-ynyl ester (1381993-89-0) → rac-efavirenz (177530-93-7,154635-17-3)

Guidance literature:

With potassium phosphate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; In toluene; at 120 ℃; for 24h; Inert atmosphere;

Reference yield:

1-(2,5-dichloro-phenyl)-2,2,2-trifluoroethanone (886371-22-8) → rac-efavirenz (177530-93-7,154635-17-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -15 - 0 °C

1.2: 1.5 h / -45 - 0 °C

2.1: ethyl acetate / 5 h / 0 - 20 °C

2.2: 18.33 h / 0 - 20 °C

3.1: potassium phosphate / copper(l) iodide; trans-N,N'-dimethyl-1,2-cyclohexyldiamine / toluene / 24 h / 120 °C / Inert atmosphere

With potassium phosphate; n-butyllithium; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; In tetrahydrofuran; hexane; ethyl acetate; toluene;

upstream raw materials:

1,1'-carbonyldiimidazole

6-amino-3-chloro-α-cyclopropylethynyl-α-(trifluoromethyl)benzyl alcohol

N-(4-chlorophenyl)-2,2-dimethylpropionamide

4-chloro-aniline

Downstream raw materials:

(R)-efavirenz

efavirenz