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

반응식

[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]

참가 물질

반응물 3

HCID 8025Ethyl formate

HCID 8471Triethylamine

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

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록: ord-655b2fb77cc04ca4953a5d16062fe106
출처 데이터셋: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09216973B2

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