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

HRID 1844631Notes

Reaction equation

HRID 1844631 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

4

Reactant 3

HCID 8025Ethyl formateHCID 8471TriethylamineHCID 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

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

Sources & evidence

ORD record
ord-eb69723505fd498caac1e8a798ab1c0f
Source dataset
uspto-grants-2015_02
Patent number
US08946447B2

Reaction notes

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