655-05-0

Basic information

• Product Name: Thozalinone
• Synonyms: Thozalinone;2-dimethylamino-5-phenyl-1,3-oxazol-4-one;Tozalinone;2-(Dimethylamino)-5-phenyl-2-oxazolin-4-one;2-(Dimethylamino)-5-phenyl-4(5H)-oxazolone;CL-39808;Stimsen;2-(dimethylamino)-5-phenyl-oxazol-4-one
• CAS NO: 655-05-0
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.22
• Mol File: 655-05-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 133-136°
• Boiling Point: 294.8 °C at 760 mmHg
• Flash Point: 132.1 °C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 0.00158mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: Thozalinone(CAS DataBase Reference)
• NIST Chemistry Reference: Thozalinone(655-05-0)
• EPA Substance Registry System: Thozalinone(655-05-0)

Safety Data

• Hazardous Substances Data: 655-05-0(Hazardous Substances Data)

Usage

Brand name

Tozalinone is INN.

InChI:InChI=1/C11H12N2O2/c1-13(2)11-12-10(14)9(15-11)8-6-4-3-5-7-8/h3-7,9H,1-2H3

Synthetic route

(RS)-mandelamide (4410-31-5, 24008-62-6, 24008-63-7, 4358-86-5) + N,N,N',N'-tetramethylchlorformamidinium chloride (56043-45-9, 13829-06-6) → 2-(dimethylamino)-5-phenyloxazol-4(5H)-one (655-05-0)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 25℃; for 2h; Reagent/catalyst; Solvent; Temperature;	88%

2-amino-5-phenyl-4-oxazolinone (2152-34-3) + dimethyl amine (124-40-3) → 2-(dimethylamino)-5-phenyloxazol-4(5H)-one (655-05-0)

Conditions	Yield
In ethanol at 125℃; for 2h;

2-amino-5-phenyl-4-oxazolinone (2152-34-3) + dimethyl sulfate (77-78-1) → 2-(dimethylamino)-5-phenyloxazol-4(5H)-one (655-05-0)

Conditions	Yield
With sodium methylate In methanol for 1h; Heating;

5-phenyl-2-thioxo-oxazolidin-4-one (19331-89-6) + dimethyl amine (124-40-3) → 2-(dimethylamino)-5-phenyloxazol-4(5H)-one (655-05-0)

Conditions	Yield
In ethanol at 105℃; for 1.5h;

NCNMe2 (1467-79-4) + hydroxy-phenyl-acetic acid ethyl ester (774-40-3, 4358-88-7) → 2-(dimethylamino)-5-phenyloxazol-4(5H)-one (655-05-0)

Conditions	Yield
(i) NaH, benzene, (ii) /BRN= 506093/; Multistep reaction;

benzaldehyde (100-52-7) + buten-(2)-yl magnesium bromide → 2-(dimethylamino)-5-phenyloxazol-4(5H)-one (655-05-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: ethanol / 1.5 h / 105 °C View Scheme

(RS)-methyl mandelate (4358-87-6) → 2-(dimethylamino)-5-phenyloxazol-4(5H)-one (655-05-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / methanol / Cooling with ice 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 25 °C View Scheme

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 25℃; for 2h; Reagent/catalyst; Solvent; Temperature;	88%

Conditions	Yield
In methanol; dichloromethane at 20℃; for 0.166667h;	76.9%

copper(II) choride dihydrate + 2-(dimethylamino)-5-phenyloxazol-4(5H)-one (655-05-0) → C22H24Cl2CuN4O4

Conditions	Yield
In methanol; dichloromethane at 20℃; for 0.166667h;	76.9%

Upstream product

• 1467-79-4 NCNMe₂ 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 4358-87-6 (RS)-methyl mandelate 
• 4410-31-5 (RS)-mandelamide 
• 56043-45-9 N,N,N',N'-tetramethylchlorformamidinium chloride 
• 19331-89-6 5-phenyl-2-thioxo-oxazolidin-4-one 
• 124-40-3 dimethyl amine 
• 2152-34-3 2-amino-5-phenyl-4-oxazolinone 
• 77-78-1 dimethyl sulfate 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Condensation of vilsmeier salts, derived from tetraalkylureas, with α-hydroxy amide derivatives: One-pot approach to synthesize 2-dialkylamino-2-oxazolin-4-ones

A novel and straightforward synthetic protocol was developed to synthesize 2-dialkylamino-2-oxazolin-4-ones from various Vilsmeier salts and α-hydroxy amides derivatives. Notably, thozalinone (3a), as a mild stimulant in tristimania and anorexic, could be synthesized simply and in a high yield using this methodology.