Benzyl Bromide → 1-Benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide

HRID 2068996

Reaction equation

HRID 2068996 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:20])[O:18][CH3:19]>C1(C)C=CC=CC=1>[Br-:1].[CH2:2]([N+:13]1[CH:14]=[CH:15][C:10]([CH3:9])=[C:11]([NH:16][C:17]([O:18][CH3:19])=[O:20])[CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 11672725Methyl N-(4-methylpyridin-3-yl)carbamate

Product 1

HCID 667702031-Benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromideYield 101.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

1-(Bromomethyl)benzene (19 g, 111 mmol, 1.10 equiv.) was added to a solution of methyl 4-methylpyridin-3-ylcarbamate (17 g, 102 mmol, 1.00 equiv.) in toluene (500 mL). The solution was stirred at about 110° C. for about 16 hours. After cooling to ambient temperature, the solids were collected by filtration and washed with toluene to afford the title product as a light brown solid (35 g; yield=97%).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe solids were collected by filtration
  3. washwashed with toluene

Sources & evidence

ORD record
ord-ed2443c1174f4ec99825d61dc5ecf2ca
Source dataset
uspto-grants-2012_10
Patent number
US08299084B2

Linked notes

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