Pyridine → Phenyl Methylcarbamate

HRID 1426995Notes

Reaction equation

Cl.CN.N1C=CC=C[CH:5]=1.Cl[NH:11][C:12](=[O:20])[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[CH3:5][NH:11][C:12](=[O:20])[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of commercially available methylamine hydrochloride (50 g, 0.74 mol), pyridine (124 mL, 1.53 mol), and N,N-dimethylformamide (500 mL) was stirred at 5° C., and commercially available phenyl chlorocarbamate (94 mL, 0.75 mol) was added dropwise over 2 hours. After the dripping was complete, the mixture was stirred under nitrogen atmosphere at room temperature for 16 hours. The reaction mixture was added to ice water (2 L) and extracted with ethyl acetate (1.5 L) twice. The organic layer was washed with water (1 L) and a saturated saline solution (300 mL). The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated. n-Heptane and ethyl acetate were added to the concentrated residue and the precipitate was collected by filteration and washed with n-heptane and tert-butyl methyl ether to obtain the title compound (74.2 g, 66%).

Workup

stirringthe mixture was stirred under nitrogen atmosphere at room temperature for 16 hours
extractionextracted with ethyl acetate (1.5 L) twice
washThe organic layer was washed with water (1 L)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated
additionn-Heptane and ethyl acetate were added to the concentrated residue
customthe precipitate was collected by filteration
washwashed with n-heptane and tert-butyl methyl ether

Sources & evidence

ORD record: ord-72ca605849d2454a8426d0b3ddfba5cb
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933099B2

Reaction notes

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