144691-18-9

Basic information

• Product Name: Butanamide, N,3,3-trimethyl-N-phenyl-
• CAS NO: 144691-18-9
• Molecular Formula: C13H19NO
• Molecular Weight: 205.3
• Mol File: 144691-18-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Butanamide, N,3,3-trimethyl-N-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanamide, N,3,3-trimethyl-N-phenyl-(144691-18-9)
• EPA Substance Registry System: Butanamide, N,3,3-trimethyl-N-phenyl-(144691-18-9)

Safety Data

• Hazardous Substances Data: 144691-18-9(Hazardous Substances Data)

Upstream product

• 7065-46-5 3,3-dimethylbutanoic acid chloride 
• 100-61-8 N-methylaniline 

Downstream Products

• 144691-20-3 2-(tert-Butyl)-3-(N-methyl-N-phenylamino)-2H-azirine 
• 72807-56-8 3,3-dimethyl-N-phenylbutanamide 
• 144691-24-7 N²-2-(Benzyloxycarbonyl)glycyl>-2-(tert-butyl)-N¹-methyl-N¹-phenylglycine-amide 
• 175467-55-7 2-tert-Butyl-3,3-diphenyl-thiirane-2-carboxylic acid methyl-phenyl-amide 
• 175467-47-7 2-Diazo-3,3,N-trimethyl-N-phenyl-butyramide 

Relevant articles and documents

Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant

An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.

Diazo-Transfer Reaction with Diphenyl Phosphorazidate

Diphenyl phosphorazidate (DPPA) was used as the azide source in a one-pot synthesis of 2,2-disubstituted 3-amino-2H-azirines 1 (Scheme 1).The reaction with lithium enolates of amides of type 2, bearing two substituents at C(2), proceeded smoothly in THF at 0 degree C; keteniminium azides C and azidoenamines D are likely intermediates.Under analogous reaction conditions, DPPA and amides of type 3 with only one substituent at C(2) gave 2-diazoamides 5 in fair-to-good yield (Scheme 2).The corresponding 2-diazo derivatives 6-8 were formed in low yield by treatment of the lithium enolates of N,N-dimethyl-2-phenylacetamide, methyl 2-phenylacetate, and benzyl phenyl ketone, respectively, with DPPA.Thermolysis of 2-diazo-N-methyl-N-phenylcarboxamides 5a and 5b yielded 3-subdtituted 1,3-dihydro-N-methyl-2H-indol-2-ones 9a and 9b, respectively (Scheme 3).The diazo compounds 5-8 reacted with 1,3-thiazole-5(4H)-thiones 10 and thiobenzophenone (13) to give 6-oxa-1,9-dithia-3-azaspironona-2,7-dienes 11 (Scheme 4) and thiirane-2-carboxylic acid derivatives 14 (Scheme 5), respectively.In analogy to previously described reactions, a mechanism via 1,3-dipolar cycloaddition, leading to 2,5-dihydro-1,3,4-thiadiazoles, and elimination of N2 to give the 'thiocarbonyl ylides' of type H or K is proposed.These dipolar intermediates with a conjugated C=O group then undergo either a 1,5-dipolar electrocyclization to give spiroheterocycles 11 or a 1,3-dipolar electrocyclization to thiiranes 14.