Ethyl formate → N-(4-bromo-3-methyl-benzyl)-formamide

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[CH3:10].C(N(CC)CC)C.[CH:18](OCC)=[O:19]>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][CH:18]=[O:19])=[CH:4][C:3]=1[CH3:10]

Participants

Reactant 3

HCID 8025Ethyl formate

HCID 8471Triethylamine

HCID 21756143(4-Bromo-3-methylphenyl)methanamine

Product 1

HCID 58497978N-(4-bromo-3-methyl-benzyl)-formamide

Procedure

To a solution of 4-bromo-3-methyl-benzylamine (15.11 g) (Example I1) in ethyl formate (150 ml) was added triethylamine (1.5 ml) at ambient temperature. The reaction mixture was stirred at reflux for 16 hours. The reaction mixture was concentrated and the residue was triturated with diisopropyl ether/heptane (1:1) (100 ml) to give N-(4-bromo-3-methyl-benzyl)-formamide (14.04 g) as a white solid. 1H-NMR (400 MHz, CDCl3): 8.28 (s, 1H), 7.49 (m, 1H), 7.16 (s, 1H), 6.97 (m, 1H), 5.85 (s, 1H), 4.42 (m, 2H), 2.39 (s, 3H) ppm.

Workup

customat ambient temperature
temperatureat reflux for 16 hours
concentrationThe reaction mixture was concentrated
customthe residue was triturated with diisopropyl ether/heptane (1:1) (100 ml)

Sources & evidence

ORD record: ord-eb69723505fd498caac1e8a798ab1c0f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946447B2

Reaction notes

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