3019-71-4

Usage

Uses

Used in Pharmaceutical Industry:
Trichloroacetyl isocyanate is used as a reagent for the conversion of alcohols to carbamates, which is an important step in the synthesis of various pharmaceutical compounds.
Used in Chemical Research:
Trichloroacetyl isocyanate is used as an in situ derivatizing reagent for the characterization of alcohols, glycols, phenols, and amines by nuclear magnetic resonance (NMR). This application is crucial for understanding the structure and properties of these compounds.
Used in Catalytic One-Pot Dehydrative Glycosylation:
Trichloroacetyl isocyanate is used in the catalytic one-pot dehydrative glycosylation of 1-hydroxy carbohydrates, which is a significant process in the synthesis of complex carbohydrate structures.
Used in the Preparation of Cefuroxime Axetil:
Trichloroacetyl isocyanate has been reported in the literature for the preparation of cefuroxime axetil, which is an antibiotic prodrug. This application highlights its importance in the development of pharmaceuticals.

Preparation

Trichloroacetyl isocyanate can be obtained by reacting 2,2,2-trichloroacetamide with oxalyl chloride. Procedure: A reaction mixture of 2,2,2-trichloroacetamide (100 g, 616 mmol, 1.0 eq) in (COCl)2 (725 g, 5.71 mol, 500 mL, 9.28 eq) was heated to 70°C for 24 hours. The reaction mixture was concentrated under vacuum. To the mixture was added 1,2,4-trichlorobenzene (500 mL) and (COCl)2 (116 g, 914 mmol, 80 mL, 1.48 eq). The reaction mixture was stirred at 100°C for 5 hours. Heat to 125°C for 15 hours. The mixture was then heated to 140°C for 5 hours. The reaction mixture was distilled under water pump (72°C-76°C fractions) to give trichloroacetyl isocyanate (60 g, 319 mmol, 52% yield) as a colorless oil.

InChI:InChI=1/C3Cl3NO2/c4-3(5,6)2(9)7-1-8

Upstream product

• 87-90-1 trichloroisocyanuric acid 
• 76-02-8 trifluoroacetyl chloride 
• 76934-15-1 C₆H₁₁Cl₂NO₃ 
• 681-99-2 tributyltin isocyanate 
• 917-61-3 sodium isocyanate 
• 76934-16-2 C₇H₁₃Cl₂NO₃ 
• 79-37-8 oxalyl dichloride 
• 594-65-0 trichloroacetamide 

Downstream Products

• 35737-62-3 (2,2,2-Trichloro-acetyl)-thiocarbamic acid S-cyclohex-1-enyl ester 
• 27046-25-9 3-benzyl-2-phenyl-6-trichloromethyl-2,3-dihydro-[1,3,5]oxadiazin-4-one 
• 40046-83-1 2-(4-nitro-phenyl)-3-phenyl-6-trichloromethyl-2,3-dihydro-[1,3,5]oxadiazin-4-one 
• 42786-14-1 6-(4-methoxy-phenyl)-2-trichloromethyl-[1,3]oxazin-4-one 
• 54683-20-4 C₁₁H₁₁Cl₃N₂O 
• 21631-77-6 5-benzoyl-2-trichloromethyl-oxazol-4-one 
• 64434-82-8 N-Trichloracetyl-O-cyclohexylurethan 
• 64434-81-7 N-Trichloracetyl-O-phenylurethan 
• 42786-13-0 6-p-tolyl-2-trichloromethyl-[1,3]oxazin-4-one 
• 69736-56-7 3-(4-methoxy-benzylideneamino)-2-(4-methoxy-phenyl)-6-trichloromethyl-2,3-dihydro-[1,3,5]oxadiazin-4-one 
• 18006-60-5 5,5-dimethyl-2-trichloromethyl-[1,3]oxazine-4,6-dione 
• 50785-76-7 2-[1-Ethoxy-meth-(Z)-ylidene]-N-(2,2,2-trichloro-acetyl)-butyramide 
• 53875-34-6 (E)-3-Phenoxy-N-(2,2,2-trichloro-acetyl)-acrylamide 
• 53875-40-4 6-p-tolylsulfanyl-2-trichloromethyl-5,6-dihydro-[1,3]oxazin-4-one 

Relevant academic research and scientific papers

KRAS G12C INHIBITORS

The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.

Process for the preparation of acyl isocyanates

The invention concerns a process for the preparation of acyl isocyanates which consists of reacting oxalyl chloride with a salt selected from the group consisting of hydrohalides and sulphates of carboxamides and/or carbamates, unsubstituted on nitrogen, then heating the reaction mixture at a temperature between 30° and 150° C. The process is suitable for preparation of acyl isocyanates with excellent yields in easy to control operational conditions.

CONDENSATION OF ACYL CHLORIDE ON SODIUM CYANATE : PREPARATION OF ACYL ISOCYANATES

The catalytic effects of various metal halides and solvents on the reaction of benzoyl chloride with sodium cyanate were studied.It has been found that SnCl4, and ZnCl2 catalyze the reaction to give the corresponding acyl isocyanates in good yields.The scope of the reaction was studied and a number of aroyl isocyanates and their derivatives were prepared.A few non aromatic isocyanates and their derivatives were also prepared.

Carbonyl Diisocyanate: A New Preparation and Some Reactions

A preparation of carbonyl diisocyanate (2) from tri-n-butyltin isocyanate (4) and phosgene is reported.Correspondingly, the acyl isocyanates 6 were obtained from 4 with acyl chlorides.On standing, carbonyl diisocyanate trimerizes reversibly to the triazine 9, which could also be prepared by independent syntheses from the triazines 3 or 12.Reported are reactions of carbonyl diisocyanate with water, hydrogen sulfide, alcohols, phenol, phenol + carbodiimides, thiols, amines, primary ammonium salts, and N-unsubstituted imines leading to compounds 14-24.

REACTIVITY OF N,N-DICHLOROURETHANES. X. ADDITION OF N,N-DICHLOROURETHANES TO VINYL ETHERS

N,N-Dichlorourethanes add readily to vinyl ethers to form alkyl N-chloro-N-(2-chloro-1-alkoxyethyl)carbamates, which are used for the production of alkyl N-(2-chloro-1-alkoxyethyl)carbamates, 2-alkoxyaziridines, 1-chloro-2-di(alkoxycarbonylamino)ethanes, 1-alkoxyperchloroethyl and 1,2,2-trichloro-1-alkoxyethyl isocyanates.