1035229-33-4|5-(Benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one| Ambeed

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Quality Control of [ 1035229-33-4 ] Purity: 95% SDS Specification

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Product Details of [ 1035229-33-4 ]

CAS No. :	1035229-33-4
Formula :	C₁₇H₁₄ClNO₄
M.W :	331.75
SMILES Code :	O=C1NC2=C(OCC3=CC=CC=C3)C=CC(C(CCl)=O)=C2OC1
MDL No. :	MFCD22575152
InChI Key :	BZZOXWZXEQFUKK-UHFFFAOYSA-N
Pubchem ID :	57989161

Safety of [ 1035229-33-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1035229-33-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1035229-33-4 ]

[ 1035229-33-4 ] Synthesis Path-Downstream 1~1

1
[ 1035229-32-3 ]
[ 1035229-33-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; acetic acid; In dichloromethane; water; at 65℃; for 20h;	Benzyltrimethylammonium dichloroiodate (14.2 g, 40.8 mmol) was added to a stirred solution of <strong>[1035229-32-3]8-acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one</strong> (5.50 g, 18.5 mmol) in a mixture of dichloromethane (100 mL), acetic acid (33 mL) and water (5.5 mL). The reaction mixture was stirred at 65 C. for 20 hours. The reaction was then cooled to room temperature, treated with aqueous sodium bisulphate (5.78 g, in 100 mL), and stirred for another 30 minutes. The mixture was diluted with ether (200 mL) and the resulting solid was filtered off, washed with water, then ether, and dried under vacuum at 40 C. to afford the title compound (5.60 g, 17.4 mmol, yield 94% yield) as a yellow solid. MS (ESI+) 332 [M+1-1]+.
89%	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; acetic acid; In dichloromethane; water; at 65℃; for 18h;Darkness;	Intermediate 15 5-Benzyioxy-8-(2-chloro-acetyl)-4f/-benzo[1 ,4]oxazin-3-one; Benzyltrimethylammonium dichloroiodate (9.27 g, 26.6 mmol) was added to a stirred solution of 8-acetyl-5-benzyloxy-4/-/-benzo[1 ,4]oxazin-3-one (3.60 g, 12.1 mmol) in a mixture of DCM (65 ml_), acetic acid (22 ml_), and water (3.6 mL) that was heated at 65 0C and protected from light, for 18 h. The reaction mixture was cooled to RT and a solution of sodium bisulphite (3.78 g) in water (65 mL) was added and mixed vigorously to form a suspension. After stirring for 0.5 h diethyl ether (150 mL) was added and the solids collected by filtration, washed with water, then ether and dried at 40 0C in vacuo to afford a light brown crystalline solid. Yield: 3.56 g (89%). LC-MS (Method 3): Rt 3.50 min, m/z 332 [M+H]+.
89%	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; acetic acid; In dichloromethane; water; at 65℃; for 18h;	intermediate 61; <n="105"/>5-Benzyloxy-8-(2-chloro-acetyl)-4H-benzo[1,4]oxazin-3-one; Benzyltrimethylammonium dichloroiodate (9.27 g, 26.6 mmol) was added to a stirred solution of 8-acetyl-5-benzyloxy-4/-/-benzo[1 ,4]oxazin-3-one (3.60 g, 12.1 mmol) in a mixture of DCM (65 ml_), acetic acid (22 ml_), and water (3.6 ml_), which was heated at 65 0C, protected from light, for 18 h. The reaction mixture was cooled to RT and a solution of sodium bisulphite (3.78 g) in water (65 ml_) was added and mixed vigorously to form a suspension. After stirring for 0.5 h diethyl ether (150 ml_) was added and the solids collected by filtration, washed with water, then ether and dried at 40 0C in vacuo to afford a light brown crystalline solid. Yield: 3.56 g (89%).LC-MS (Method 4): Rt 3.50 min, m/z 332 [M+H]+.

		Step v) 5-(Benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b] [1 ,4]oxazin-3(4H)-oneBenzyltrimethylamnionium dichloroiodate (14.17 g) was added to a stirred solution of 8- acetyl-5-(benzyloxy)-2H-benzo[b][l,4]oxazin-3(4H)-one (5.5 g) [Step iv] in a mixture of dichloromethane (100 mL), AcOH (33 mL) and water (5.5 niL) and the reaction mixture stirred at 65 0C for 20 h. The reaction was cooled to ambient temperature, treated with aqueous sodium bisulphite (5.78 g in 100 mL) and stirred for a further 30 minutes. The mixture was diluted with diethylether (200 mL) and the resulting solid filtered off, washed with water and furtehr diethylether, and dried under vacuum at 40 0C to afford the subtitled compound as a light brown solid (5.6 g).1U NMR (299.947 MHz, DMSO) delta 10.41 (s, IH), 7.55 (m, 2H), 7.44 (d, J = 9.4 Hz, IH), 7.39 (m, 2H), 7.32 (m, IH), 6.95 (d, J = 9.4 Hz, IH), 5.30 (s, 2H), 4.96 (s, 2H), 4.69 (s, 2H).
	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; In ethanol; for 1h;Reflux;Product distribution / selectivity;	Step v) 5-(Benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b] [ 1 ,4]oxazin-3(4H)-one The solvent can be changed from dichloromethane, acetic acid and water to ethanol/water leading to the product precipitating directly rather then needing an extractive work-up. With this procedure there is no need to use an aqueous sodium bisulfite wash. For example:To the product from Preparation 2 Step iv) (23 g) and benzyltrimethylammonium dichloroiodate (53.85 g) was added ethanol (230 mL). The mixture was heated at reflux for 1 h then cooled to 500C and water (230 mL) added. The mixture was cooled to 200C and stirred for at least 1 h. The suspension was filtered, washed with water (46 mL) and then ethanol (69 mL). To the damp solid was added ethyl acetate (460 mL). The mixture was heated at reflux for 1 h then cooled to 200C and stirred for at least 1 h. The suspension was filtered and the residue was washed with ethyl acetate (115 mL) and dried under vacuum to yield the sub-titled compound (61.0 g).

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .Location in patent: Paragraph 0117.
[3]Patent: WO2010/15792,2010,A1 .Location in patent: Page/Page column 49-50.
[4]Patent: WO2008/149110,2008,A1 .Location in patent: Page/Page column 103-104.
[5]Patent: WO2008/75025,2008,A1 .Location in patent: Page/Page column 86.
[6]Patent: WO2009/154557,2009,A1 .Location in patent: Page/Page column 37.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Nomenclature of Ethers • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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[ 1035229-33-4 ]

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CAS No.: 1035229-33-4

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