71526-50-6

Basic information

• Product Name: 6-Chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one
• Synonyms: 6-Chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one
• CAS NO: 71526-50-6
• Molecular Weight: 335.79
• Mol File: 71526-50-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-Chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one(71526-50-6)
• EPA Substance Registry System: 6-Chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one(71526-50-6)

Safety Data

• Hazardous Substances Data: 71526-50-6(Hazardous Substances Data)

Upstream product

• 18928-48-8 5-Chloro-2-isocyanatobenzoyl chloride 
• 71-43-2 benzene 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 134-20-3 2-carbomethoxyaniline 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 36192-63-9 2-amino-4'-methylbenzophenone 
• 111838-36-9 4-ethoxy-4-phenyl-1,4-dihydro-3,1-benzoxazin-2(1H)-one 
• 62-53-3 aniline 
• 91148-63-9 4-methoxy-4-phenyl-1,2-dihydro-3,1-benzoxazine-2(4H)-one 
• 5100-23-2 2-isocyanatobenzoyl chloride 
• 100-58-3 phenylmagnesium bromide 

Relevant articles and documents

Friedel-Crafts Acylation with 2-Isocyanatobenzoyl Chlorides: The Structure of the Intermediate Complex

The intermediate complex obtained in the Friedel-Crafts acylation of benzene with 2-isocyanatobenzoyl chloride (1a) reacts with methanol or ethanol in the presence of ether affording 4-alkoxy-4-phenyl-1,4-dihydro-3,1-benzoxazin-2(1H)-ones, whereas with anilines, the corresponding anils of 2-aminobenzophenone are obtained.In the presence of triethylamine, the complex reacts with aniline and 2-aminobenzophenone affording 4-hydroxy-4-phenyl-3-substituted 3,4-dihydroquinazolin-2(1H)-ones whereas, with alkyl anthranilates, the new 11b-phenyl-7,11b-dihydroquinazolinobenzoxazine-6,13-diones are obtained.Similar products are also obtained from 5-chloro-2-isocyanatobenzoyl chloride.The intermediate complex has been shown to exist exclusively in the cyclic form in both acidic and basic media.

Reactions of 2-Isocyanatobenzoyl Chlorides with Phenylmagnesium Bromide: Synthesis of 2-Phenyl-3,1-benzoxazin-4(H)-ones, N-Benzoyl-2-aminobenzophenones, α-(2-Benzamidoaryl)benzohydrols and 6-Chloro-4,4-diphenyl-3,1-benzoxazin-2(4H)-one

In the reaction of 2-isocyanatobenzoyl chloride (Ia) with phenylmagnesium bromide, the isocyanato group is found to be exclusively attacked by the Grignard reagent to give 2-phenyl-3,1-benzoxazin-4(H)-one (IIIa), N-benzoylanthranilic acid (IVa), N-benzoyl-2-aminobenzophenone (Va), and α-(2-benzamidophenyl)benzohydrol (VIa) depending on the mode of addition and the relative amounts of the Grignard reagent.However, in the case of 5-chloro-2-isocyanatobenzoyl chloride (Ib), the chloroformyl group is also found to react simultaneously, although to a smaller extent, to give 6-chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one (VIIb) in addition to 6-chloro-2-phenyl-3,1-benzoxazin-4(H)-one (IIIb), N-benzoyl-2-amino-5-chlorobenzophenone (Vb) and α-(2-benzamido-5-chlorophenyl)benzohydrol (VIb) depending on the reaction conditions.This is presumably due to the decreased reactivity of the isocyanato function due to the chloro group in the para-position.The reaction is believed to proceed through an acyclic intermediate complex which affords IIIa on work-up.PMR data of the compounds have also been discussed.