N-(4-Chlorobenzoyl)glycine
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N-(4-Chlorobenzoyl)glycine
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CAS No:
13450-77-6
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Formula:
C9H8ClNO3
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Chemical Name:
N-(4-Chlorobenzoyl)glycine
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Synonyms:
Glycine,N-(4-chlorobenzoyl)-;Hippuric acid,p-chloro-;N-(4-Chlorobenzoyl)glycine;p-Chlorohippuric acid;4-Chlorohippuric acid;p-Chlorobenzoylglycine;N-(p-Chlorobenzoyl)glycine;4-Chlorobenzoylglycine;Ro 11-1903;2-(4-Chlorobenzamido)aceticacid;2-[(4-Chlorophenyl)formamido]acetic acid;2-(4-Chlorobenzamido)acetic acid;80353-60-2
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CAS No:
Safety Information
IRRITANT
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
N-(4-Chlorobenzoyl)glycine Use and Manufacturing
A solution of ethyl (4-chlorobenzoyl) glycine (2.21 mmol, 0.535 g) in 15 ml of THF: MeOH: H2O (3: 1: 1)Lithium hydroxide (4.43 mmol, 0.106 g) was added, The reaction was allowed to proceed overnight at room temperature.The solvent was distilled off under reduced pressure, 20 ml of ethyl acetate and water were added thereto, respectively, The aqueous phase was separated, The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to give a white solid in 85percent yield.In a 500 mL round bottom flask, a stirred solution of methyl 2-(4- chlorobenzamido) acetate (20 g, 88.1 mmol) in THF (100 mL), methanol (100 mL) and water (100 mL) was treated with lithium hydroxide monohydrate (18.5 g, 441 mmol) at RT. The reaction mixture was stirred at RT for 12 h. Upon completion of reaction (TLC), the reaction mixture was concentrated under reduced pressure. The residue obtained was washed with EtOAc, diluted with cold water and acidified (pH ~ 5) with 1 N HC1. The solid was filtered and dried under reduced pressure to give the title compound (14.21 g, 75.6percent). (0353) 1H NMR (300 MHz, DMSO-dTo a stirred and cooled (15 °C) solution of glycine (5.0 g, 66.602 mmol) in 10percent aqueous sodium hydroxide solution (50 mL) was added benzoyl chloride (11.8 mL, 92.57 mmol) in portions. The reaction mixture was stirred at RT for 1.5 h. The reaction mixture was poured in to crushed ice and acidified with conc. HC1 till pH 3-4.The obtained precipitate was collected by filtration and dried to yield 11.2 g of thetitle product as a solid. ‘H NMR (300 MHz, DMSO-d6) ö 4.08 (s, 2H), 7.49 (d, J = 8.7Hz, 2H), 7.85 (d, J = 8.1 Hz, 2H), 8.00 (d, J = 8.4 Hz, 1H).
Computed Properties
Molecular Weight:213.62
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:213.0192708
Monoisotopic Mass:213.0192708
Topological Polar Surface Area:66.4
Heavy Atom Count:14
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes