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

HRID 1505267Notes

Reaction equation

HRID 1505267 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 (Example 10.1) (15.11 g) 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. temperatureat reflux for 16 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was triturated with diisopropyl ether/heptane (1:1) (100 ml)

Sources & evidence

ORD record
ord-655b2fb77cc04ca4953a5d16062fe106
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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