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

反応式

[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]

参加物

反応物 3

HCID 8025Ethyl formate

HCID 8471Triethylamine

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

生成物 1

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

実験手順

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.

後処理

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)

出典と根拠

ORDレコード: ord-eb69723505fd498caac1e8a798ab1c0f
出典データセット: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08946447B2

反応ノート

読み込み中…

参加物